Publications
In this page you can find our publications, from latest to oldest.
2022
Panza, N.; Alberti, M.; Galiè, S.; Damiano, C.; Cargnoni, F.; Trioni, M. Italo; Caselli, A.
Ammonium Ferrate-Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3-Oxazolidin-2-ones Journal Article
In: European Journal of Organic Chemistry, vol. 2022, no. 40, 2022, ISSN: 1434193X.
@article{Panza2022,
title = {Ammonium Ferrate-Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3-Oxazolidin-2-ones},
author = {N. Panza and M. Alberti and S. Galiè and C. Damiano and F. Cargnoni and M. Italo Trioni and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85140709299&doi=10.1002%2fejoc.202200908&partnerID=40&md5=1886cd498ff54ddf13b2c3c03fec5e2c},
doi = {10.1002/ejoc.202200908},
issn = {1434193X},
year = {2022},
date = {2022-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2022},
number = {40},
publisher = {John Wiley and Sons Inc},
abstract = {Simple ammonium ferrates are competent catalysts for the CO2 coupling with aziridines to yield 5-substituted 1,3-oxazolidin-2-ones. Good yields with remarkable selectivity are obtained under mild reaction conditions, room temperature, and atmospheric CO2 pressure, especially for non-hindered N-alkyl, N-benzyl and N-allyl aziridines, without the need of any co-catalyst. To shed light on the reaction mechanism, an extensive set of theoretical calculations has been carried out. A viable reaction mechanism involving just one ferrate molecule and where the rate determining step is the 1,3-oxazolidin-2-one ring closure has been found, and the corresponding barrier is compatible with the experimental conditions tested in this study. © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Panza, N.; Biase, A.; Caselli, A.
Structural and spectroscopical characterization of µ-oxo bridged Iron(III) bromide complexes of Pyclen ligands Journal Article
In: Inorganica Chimica Acta, vol. 541, 2022, ISSN: 00201693.
@article{Panza2022b,
title = {Structural and spectroscopical characterization of µ-oxo bridged Iron(III) bromide complexes of Pyclen ligands},
author = {N. Panza and A. Biase and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85134698562&doi=10.1016%2fj.ica.2022.121091&partnerID=40&md5=b0e9d2d16494586fcd0658023b70ff6b},
doi = {10.1016/j.ica.2022.121091},
issn = {00201693},
year = {2022},
date = {2022-01-01},
journal = {Inorganica Chimica Acta},
volume = {541},
publisher = {Elsevier B.V.},
abstract = {Binuclear iron oxo-bridged complexes have found much interest since the early 80′s as synthetic models for relevant biological molecules, catalysts and magnetic probes. In this work, a series of iron(III)bromide-based oxo-bridged complexes of Pyclen ligands was prepared, with the aim of investigating the peculiar iron-oxygen bond features in different molecular environments. We observed the influence of the steric hindrance of the ligands employed in this study towards the formation of symmetrical and non-symmetrical µ-oxo complexes, and we confirmed this peculiar behaviour by single crystal X-ray diffraction and Raman spectroscopy. We report here structural and spectroscopical insight of three unprecedented oxo-iron complexes and their relative precursors, enlarging the existing database of these particular class of metal complexes. © 2022 Elsevier B.V.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Brambilla, E.; Bortolla, A.; Pirovano, V.; Caselli, A.; Tiecco, M.; Abbiati, G.
In: Applied Organometallic Chemistry, vol. 36, no. 6, 2022, ISSN: 02682605.
@article{Brambilla2022,
title = {Silver-catalysed A3-coupling reactions in phenylacetic acid/alkylamine N-oxide eutectic mixture under dielectric heating: An alternative approach to propargylamines},
author = {E. Brambilla and A. Bortolla and V. Pirovano and A. Caselli and M. Tiecco and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85126807821&doi=10.1002%2faoc.6669&partnerID=40&md5=ae9416c525ee7ee1aff83e7784cb599d},
doi = {10.1002/aoc.6669},
issn = {02682605},
year = {2022},
date = {2022-01-01},
journal = {Applied Organometallic Chemistry},
volume = {36},
number = {6},
publisher = {John Wiley and Sons Ltd},
abstract = {The development of alternative benign reaction conditions to perform multicomponent reactions is an interesting and desirable strategy to increase the sustainability of organic synthesis. In this paper, we report a new version of A3-coupling MCR for the preparation of differently substituted propargylamines starting from aldehydes, alkynes and amines in an acidic DES as reaction media, under dielectric heating, and in the presence of a tetraaza-macrocyclic silver complex as catalyst. The reaction scope is broad in terms of aldehyde partners. Electron-rich phenylacetylenes are the more reactive alkynes partners, whereas the nature of the amine is the more serious limitation as only secondary cyclic amines are tolerated. © 2022 The Authors. Applied Organometallic Chemistry published by John Wiley & Sons Ltd.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Brambilla, E.; Abbiati, G.; Caselli, A.; Pirovano, V.; Rossi, E.
Coinage metal carbenes in heterocyclic synthesis via formation of new carbon-heteroatom bonds Journal Article
In: Tetrahedron, vol. 114, 2022, ISSN: 00404020.
@article{Brambilla2022b,
title = {Coinage metal carbenes in heterocyclic synthesis via formation of new carbon-heteroatom bonds},
author = {E. Brambilla and G. Abbiati and A. Caselli and V. Pirovano and E. Rossi},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85129011110&doi=10.1016%2fj.tet.2022.132778&partnerID=40&md5=92ec4281e825d336790132c646a63990},
doi = {10.1016/j.tet.2022.132778},
issn = {00404020},
year = {2022},
date = {2022-01-01},
journal = {Tetrahedron},
volume = {114},
publisher = {Elsevier Ltd},
abstract = {The review describes the most recently reported and efficient methods for the synthesis of heterocyclic compounds involving metal carbenes. In particular, copper, silver and gold carbenes, generated from suitable precursors, are involved in the synthesis of heterocyclic compounds through the formation of new carbon-heteroatom bonds. © 2022 Elsevier Ltd},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Panza, N.; Tseberlidis, G.; Caselli, A.; Vicente, R.
Recent progress in the chemistry of 12-membered pyridine-containing tetraazamacrocycles: from synthesis to catalysis Journal Article
In: Dalton Transactions, vol. 51, no. 28, pp. 10635-10657, 2022, ISSN: 14779226.
@article{Panza202210635,
title = {Recent progress in the chemistry of 12-membered pyridine-containing tetraazamacrocycles: from synthesis to catalysis},
author = {N. Panza and G. Tseberlidis and A. Caselli and R. Vicente},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85128767031&doi=10.1039%2fd2dt00597b&partnerID=40&md5=002d357fa508e3a95b369c57c92e3d6c},
doi = {10.1039/d2dt00597b},
issn = {14779226},
year = {2022},
date = {2022-01-01},
journal = {Dalton Transactions},
volume = {51},
number = {28},
pages = {10635-10657},
publisher = {Royal Society of Chemistry},
abstract = {This article provides an overview (non-comprehensive) of the recent developments regarding pyridine-containing 12-membered tetraazamacrocycles with pyclen or Py2N2 backbones and their metal complexes from 2017 to the present. Firstly, the syntheses of newly described ligands and complexes with relevance to medicine are described. The second part deals with the reactivity of complexes bearing these ligands and their uses in catalysis. Special emphasis on the role of the pyridine-containing ligand is highlighted throughout the text. © 2022 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Galluzzi, M.; Marfori, L.; Asperti, S.; Vita, A. De; Giannangeli, M.; Caselli, A.; Milani, P.; Podestà, A.
Interaction of imidazolium-based ionic liquids with supported phospholipid bilayers as model biomembranes Journal Article
In: Physical Chemistry Chemical Physics, vol. 1, 2022, ISSN: 14639076.
@article{Galluzzi2022,
title = {Interaction of imidazolium-based ionic liquids with supported phospholipid bilayers as model biomembranes},
author = {M. Galluzzi and L. Marfori and S. Asperti and A. De Vita and M. Giannangeli and A. Caselli and P. Milani and A. Podestà},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85142284978&doi=10.1039%2fd2cp02866b&partnerID=40&md5=94d873080365e3bce680f292a89961a2},
doi = {10.1039/d2cp02866b},
issn = {14639076},
year = {2022},
date = {2022-01-01},
journal = {Physical Chemistry Chemical Physics},
volume = {1},
publisher = {Royal Society of Chemistry},
abstract = {The cytotoxicity of ionic liquids (ILs) has been receiving attention in the context of the biological and environmental impact of their vast field of applications. It has been ascertained that the cell membrane is the main target of ILs when they interact with microorganisms, cells and bacteria; nevertheless, studies at the micro- and nano-scale aiming at better understanding of the fundamental mechanisms of toxicity of ILs are lacking. In this work, we used atomic force microscopy (AFM) to investigate the impact of room-temperature ILs on the mechanical, morphological and electrostatic properties of solid-supported DOPC phospholipid bilayers, taken as models of biomembranes. In particular, we have characterized the concentration-dependent and time-dependent evolution of the morphological, structural and mechanical properties of DOPC lipid membranes in the presence of imidazolium-based ILs with different alkyl chain lengths and hydrophilic/hydrophobic characteristics. The majority of ILs investigated were found to possess the ability of restructuring the lipid bilayer, through the formation of new IL/lipid complexes, showing distinctive morphological features (increase of area and roughness). The nanomechanical analysis of the lipid membrane exposed to ILs revealed a progressive, concentration-dependent perturbation of the structural ordering and rigidity of the membrane, evidenced by a decrease in the breakthrough force, Young's modulus and area stretching modulus. AFM detected a modification of the electrostatic double-layer at the membrane surface, in terms of a reduction of the original negative surface charge density, suggesting a progressive stratification of cations on the exposed leaflet of the lipid membrane. Our findings may be helpful in designing novel ILs with tailored interaction with biological membranes. © 2022 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Panza, N.; Soave, R.; Cargnoni, F.; Trioni, M. I.; Caselli, A.
Experimental and theoretical insight into the mechanism of CO2cycloaddition to epoxides catalyzed by ammonium ferrates Journal Article
In: Journal of CO2 Utilization, vol. 62, 2022, ISSN: 22129820.
@article{Panza2022d,
title = {Experimental and theoretical insight into the mechanism of CO2cycloaddition to epoxides catalyzed by ammonium ferrates},
author = {N. Panza and R. Soave and F. Cargnoni and M. I. Trioni and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85131767982&doi=10.1016%2fj.jcou.2022.102062&partnerID=40&md5=162355a5f138c18f8e26203a19b38606},
doi = {10.1016/j.jcou.2022.102062},
issn = {22129820},
year = {2022},
date = {2022-01-01},
journal = {Journal of CO2 Utilization},
volume = {62},
publisher = {Elsevier Ltd},
abstract = {Soluble tetrabutylammonium ferrates, [TBA][FeX3Y] (TBA = nBu4N) were synthetized by treating ferric salts (FeX3) with tetrabuthylammoniom halides. Their activity as a stand-alone catalyst in CO2 cycloaddition reactions to epoxides was assessed under solvent free and quite mild reaction conditions (CO2 pressures between 0.4 and 0.8 MPa) and TOF up to 428 h-1 (T = 150 °C) were observed. Good yields of cyclic organic carbonates were obtained, especially with terminal epoxides, without the need of any Lewis base as co-catalyst, with a broad reaction scope. A scale-up reaction on 5 mL of styrene oxide was performed and the robustness of the catalyst was proved up to three recycles in the case of propylene oxide (TON = 594). To shed light on the reaction mechanism, an extensive set of theoretical calculations has been carried out. Iron salts almost annihilate the barrier for the epoxide ring opening and stabilize the first reaction intermediate. Along the same reaction path, chloride proved to be more effective as nucleophile than bromide, and preferentially attacks on the more hindered carbon atom. On the other hand, when no Lewis acid (LA) is present, the rate determining step of the reaction becomes the ring opening of the epoxide. A tight correlation with experimental results was observed. © 2022 Elsevier Ltd.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Panza, N.; Alberti, M.; Damiano, C.; Caselli, A.
Ammonium zincates as suitable catalyst for the room temperature cycloaddition of CO2 to epoxides Journal Article
In: Frontiers in Catalysis, vol. 2, 2022, ISSN: 2673-7841.
@article{10.3389/fctls.2022.991270,
title = {Ammonium zincates as suitable catalyst for the room temperature cycloaddition of CO2 to epoxides},
author = {N. Panza and M. Alberti and C. Damiano and A. Caselli},
url = {https://www.frontiersin.org/articles/10.3389/fctls.2022.991270},
doi = {10.3389/fctls.2022.991270},
issn = {2673-7841},
year = {2022},
date = {2022-01-01},
urldate = {2022-01-01},
journal = {Frontiers in Catalysis},
volume = {2},
abstract = {We have recently shown that simple ammonium ferrates are competent catalyst for the cycloaddition reaction of CO_{2} to epoxides under moderate reaction conditions (T = 100°C, P(CO_{2}) = 0.8 MPa). We report here that ammonium zincates of general formulae [TBA]_{2} [ZnX_{4}] (TBA = tetrabutylammonium), simply obtained by treating an ethanolic solution of an appropriate zinc(II) salt with two equivalents of tetrabutylammonium halides, outperform ammonium ferrates in the synthesis of cyclic carbonates under milder reaction conditions (room temperature and atmospheric CO_{2} pressure). Using [TBA]_{2}[ZnBr_{4}] complex as homogeneous catalyst at 100°C and P(CO_{2}) = 0.8 MPa a 52% conversion of styrene oxide with complete selectivity in styrene carbonate in just 15 min was observed, corresponding to a Turnover frequency (TOF) of 416 h^{−1}. The same catalyst proved to be very active even at room temperature and atmospheric or very moderate CO_{2} pressures (0.2 MPa), with a quite broad range of substrates, especially in the case of terminal epoxides, with high selectivity towards cyclic carbonate products. The difference in reactivity of terminal and internal epoxides could be exploited using 4-vinylcyclohexene dioxide, where the endocyclic epoxide remained untouched when reacted at room temperature and the formation of the di-carbonate product was observed only at harsher conditions. A multigram scale conversion of propylene oxide was achieved (46 mmol) and the catalyst also proved to be recyclable (3 cycles) by distillation of the product and subsequent addition of fresh reagent, maintaining high conversion values and complete selectivity for propylene carbonate. This simple zinc-based catalytic system, which outperform the recently reported iron-based one by working at much milder conditions, could represent a valuable prospect in both laboratory and industrial scale, combining an inherent cheapness and synthetic easiness that should be deeply considered when the goal is to give value to a waste product as CO_{2}.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2021
Falchi, F. A.; Borlotti, G.; Ferretti, F.; Pellegrino, G.; Raneri, M.; Schiavoni, M.; Caselli, A.; Briani, F.
Sanguinarine Inhibits the 2-Ketogluconate Pathway of Glucose Utilization in Pseudomonas aeruginosa Journal Article
In: Frontiers in Microbiology, vol. 12, 2021, ISSN: 1664302X.
@article{Falchi2021,
title = {Sanguinarine Inhibits the 2-Ketogluconate Pathway of Glucose Utilization in Pseudomonas aeruginosa},
author = {F. A. Falchi and G. Borlotti and F. Ferretti and G. Pellegrino and M. Raneri and M. Schiavoni and A. Caselli and F. Briani},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85115694468&doi=10.3389%2ffmicb.2021.744458&partnerID=40&md5=ff0e0cb7f11f88a831d0e122ac46820e},
doi = {10.3389/fmicb.2021.744458},
issn = {1664302X},
year = {2021},
date = {2021-01-01},
journal = {Frontiers in Microbiology},
volume = {12},
publisher = {Frontiers Media S.A.},
abstract = {Interfering with the ability of pathogenic bacteria to import glucose may represent a new promising antibacterial strategy, especially for the treatment of infections occurring in diabetic and other hyperglycemic patients. Such patients are particularly susceptible to infections caused by a variety of bacteria, among which opportunistic pathogens like Pseudomonas aeruginosa. In P. aeruginosa, glucose can be directly imported into the cytoplasm or after its periplasmic oxidation into gluconate and 2-ketogluconate (2-KG). We recently demonstrated that a P. aeruginosa mutant lacking the 2-KG transporter KguT is less virulent than its kguT+ parental strain in an insect infection model, pointing to 2-KG branch of glucose utilization as a possible target for anti-Pseudomonas drugs. In this work, we devised an experimental protocol to find specific inhibitors of the 2-KG pathway of P. aeruginosa glucose utilization and applied it to the screening of the Prestwick Chemical Library. By exploiting mutants lacking genes involved in the transport of glucose derivatives in the primary screening and in the secondary assays, we could identify sanguinarine as an inhibitor of 2-KG utilization. We also demonstrated that sanguinarine does not prevent 2-KG formation by gluconate oxidation or its transport, suggesting that either KguD or KguK is the target of sanguinarine in P. Aeruginosa. © Copyright © 2021 Falchi, Borlotti, Ferretti, Pellegrino, Raneri, Schiavoni, Caselli and Briani.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Panza, N.; Biase, A.; Gallo, E.; Caselli, A.
Unexpected “ferrate” species as single-component catalyst for the cycloaddition of CO2 to epoxides Journal Article
In: Journal of CO2 Utilization, vol. 51, 2021, ISSN: 22129820.
@article{Panza2021,
title = {Unexpected “ferrate” species as single-component catalyst for the cycloaddition of CO2 to epoxides},
author = {N. Panza and A. Biase and E. Gallo and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85109172639&doi=10.1016%2fj.jcou.2021.101635&partnerID=40&md5=b3a4f57b0b365ea7790fbc56cef440fb},
doi = {10.1016/j.jcou.2021.101635},
issn = {22129820},
year = {2021},
date = {2021-01-01},
journal = {Journal of CO2 Utilization},
volume = {51},
publisher = {Elsevier Ltd},
abstract = {A soluble ferrate salt was synthetized by treating a novel protonated pyridine-containing macrocyclic ligand with iron(III) bromide. Its good activity as a stand-alone catalyst in CO2 cycloaddition reactions to epoxides was assessed. Good yields of cyclic organic carbonates were obtained, especially with terminal epoxides, under solvent-free reaction conditions (T = 100 °C, P (CO2) = 0.8 MPa), without the need of any Lewis base as the co-catalyst. This system proved to be active and selective towards the cyclic carbonates formation, with a broad reaction scope. A scale-up reaction on 2.5 mL of propylene oxide was performed and the robustness of the catalyst was proved up to three recycles (TON = 1020). © 2021 Elsevier Ltd},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Brambilla, E.; Giannangeli, M.; Pirovano, V.; Rossi, E.; Caselli, A.; Abbiati, G.
Synthesis and photophysical evaluation of polarity sensitive push-pull isoquinolines and their alkynyl precursors Journal Article
In: Organic and Biomolecular Chemistry, vol. 19, no. 22, pp. 4958-4968, 2021, ISSN: 14770520.
@article{Brambilla20214958,
title = {Synthesis and photophysical evaluation of polarity sensitive push-pull isoquinolines and their alkynyl precursors},
author = {E. Brambilla and M. Giannangeli and V. Pirovano and E. Rossi and A. Caselli and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85107772054&doi=10.1039%2fd1ob00572c&partnerID=40&md5=96d01f7501cedf2e6225d8bc82dff73c},
doi = {10.1039/d1ob00572c},
issn = {14770520},
year = {2021},
date = {2021-01-01},
journal = {Organic and Biomolecular Chemistry},
volume = {19},
number = {22},
pages = {4958-4968},
publisher = {Royal Society of Chemistry},
abstract = {Two sets of unprecedented push-pull isoquinolines, characterized by an opposite “dipolar moment” with respect to the longitudinal axis of the molecule, have been prepared. The key step of the approach is the microwave-promoted domino imination/cycloisomerization of 2-alkynyl benzaldehydes in the presence of methanolic ammonia. Absorption spectra and emission spectra of the D-π-A isoquinolines and their alkynyl precursors in nine different solvents have been recorded. The absolute QYs of all compounds have been recorded in three solvents with different polarities,i.e.toluene, DMSO and ethanol. Among the D-π-A isoquinolines prepared - nicknamed QuinaChroms - two compounds characterized by opposite dipolar moments,i.e.3-(4-methoxyphenyl)-7-nitroisoquinoline1aandN,N-diethyl-3-(4-(methylsulfonyl)phenyl)isoquinolin-7-amine2bdisplayed more interesting photophysical profiles, whereas 5-(diethylamino)-2-(A)arylethynylbenzaldehydes precursors8a-c- having a free aldehyde group that is suitable for possible conjugation − exhibited strong fluorescence and wide Stokes shifts. These products are interesting for potential use as polarity-sensitive fluorescent probes or advanced functional materials. © The Royal Society of Chemistry 2021.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Cavalleri, M.; Panza, N.; Biase, A.; Tseberlidis, G.; Rizzato, S.; Abbiati, G.; Caselli, A.
[Zinc(II)(Pyridine-Containing Ligand)] Complexes as Single-Component Efficient Catalyst for Chemical Fixation of CO2 with Epoxides Journal Article
In: European Journal of Organic Chemistry, vol. 2021, no. 19, pp. 2764-2771, 2021, ISSN: 1434193X.
@article{Cavalleri20212764,
title = {[Zinc(II)(Pyridine-Containing Ligand)] Complexes as Single-Component Efficient Catalyst for Chemical Fixation of CO2 with Epoxides},
author = {M. Cavalleri and N. Panza and A. Biase and G. Tseberlidis and S. Rizzato and G. Abbiati and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85108278570&doi=10.1002%2fejoc.202100409&partnerID=40&md5=66d0736296a6f6a641805b3d6acec547},
doi = {10.1002/ejoc.202100409},
issn = {1434193X},
year = {2021},
date = {2021-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2021},
number = {19},
pages = {2764-2771},
publisher = {John Wiley and Sons Inc},
abstract = {The reaction between epoxides and CO2 to yield cyclic carbonates is efficiently promoted under solvent-free and relatively mild reaction conditions (0.5 mol % catalyst loading, 0.8 MPa, 125 °C) by zinc(II) complexes of pyridine containing macrocyclic ligands (Pc−L pyridinophanes). The zinc complexes have been fully characterized, including X-ray structural determination. The [Zn(II)X(Pc−L)]X complexes showed good solubility in several polar solvents, including cyclic carbonates. The scope of the reaction under solvent-free conditions has been studied and good to quantitative conversions with excellent selectivities have been obtained, starting from terminal epoxides. When solvent-free conditions were not possible (solid epoxides or low solubility of the catalyst in the oxirane) the use of cyclic carbonates as solvents has been successfully investigated. The remarkable stability of the catalytic system has been demonstrated by a series of consecutive runs. © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Damiano, C.; Sonzini, P.; Caselli, A.; Gallo, E.
Imido complexes of groups 8–10 active in nitrene transfer reactions Journal Article
In: Advances in Organometallic Chemistry, vol. 76, pp. 145-184, 2021, ISSN: 00653055.
@article{Damiano2021145,
title = {Imido complexes of groups 8–10 active in nitrene transfer reactions},
author = {C. Damiano and P. Sonzini and A. Caselli and E. Gallo},
editor = {Perez P.J.},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85106425531&doi=10.1016%2fbs.adomc.2021.04.002&partnerID=40&md5=15d02aa8400a2f23f63d5ff8cf44a120},
doi = {10.1016/bs.adomc.2021.04.002},
issn = {00653055},
year = {2021},
date = {2021-01-01},
journal = {Advances in Organometallic Chemistry},
volume = {76},
pages = {145-184},
publisher = {Academic Press Inc.},
abstract = {Metal imido complexes, generally indicated as LnM[dbnd]NR, are considered key-intermediates in nitrene transfer reactions, which are efficient and atom-economic procedures for the synthesis of N-containing compounds. The isolation and characterization of catalytically active imido complexes are usually difficult tasks due to their high chemical reactivity and consequently the molecular structure of these species has often been predicted by theoretical calculations. This chapter provides an overview of imido derivatives of groups 8–10 whose structural features confer them an optimal stability/reactivity relationship. The effect of both ligand and nitrene functionality on defining the chemical characteristics of isolable active imido species will be discussed in order to rationalize how to reach the best compromise between chemical stability and catalytic activity of these class of compounds. © 2021 Elsevier Inc.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2020
Panza, N.; Biase, A.; Rizzato, S.; Gallo, E.; Tseberlidis, G.; Caselli, A.
Catalytic Selective Oxidation of Primary and Secondary Alcohols Using Nonheme [Iron(III)(Pyridine-Containing Ligand)] Complexes Journal Article
In: European Journal of Organic Chemistry, vol. 2020, no. 42, pp. 6635-6644, 2020, ISSN: 1434193X.
@article{Panza20206635,
title = {Catalytic Selective Oxidation of Primary and Secondary Alcohols Using Nonheme [Iron(III)(Pyridine-Containing Ligand)] Complexes},
author = {N. Panza and A. Biase and S. Rizzato and E. Gallo and G. Tseberlidis and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85094111788&doi=10.1002%2fejoc.202001201&partnerID=40&md5=d05683891810bffc887a659bafeed00e},
doi = {10.1002/ejoc.202001201},
issn = {1434193X},
year = {2020},
date = {2020-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2020},
number = {42},
pages = {6635-6644},
publisher = {Wiley-VCH Verlag},
abstract = {The selective oxidation of different primary and secondary alcohols to carbonyl compounds by hydrogen peroxide was found to be catalyzed in conversion ranging from good to excellent by an iron(III) complex of a pyridine-containing macrocyclic ligand (Pc-L), without the need of any additive. The choice of the counteranion (Cl, Br, OTf) appeared to be of fundamental importance and the best results in terms of selectivity (up to 99 %) and conversion (up to 98 %) were obtained using the well-characterized [Fe(III)(Br)2(Pc-L)]Br complex, 4c. Magnetic moments in solid-state, also confirmed in solution ([D6]DMSO) by Evans NMR method, were calculated and point out to an iron metal center in the high spin state of 5/2. The crystal structure shows that the iron(III) center is coordinated by the four nitrogen atoms of the macrocycle and two bromide anions to form a distorted octahedral coordination environment. The catalytic oxidation of benzyl alcohol in acetonitrile was found occurring with better conversions and selectivities than in other solvents. The reaction proved to be quite general, tolerating aromatic and aliphatic alcohols, although very low yields were obtained for terminal aliphatic alcohols. Preliminary mechanistic studies are in agreement with a catalytic cycle promoted by a high-spin iron complex. © 2020 Wiley-VCH GmbH},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Pirovano, V.; Caselli, A.; Colombo, A.; Dragonetti, C.; Giannangeli, M.; Rossi, E.; Brambilla, E.
In: ChemCatChem, vol. 12, no. 20, pp. 5250-5255, 2020, ISSN: 18673880.
@article{Pirovano20205250,
title = {Synthesis of 2-alkenylidene-3-oxoindolines: cascade reactions of 4H-furo [3,2-b]indoles with diazoacetates catalyzed by a Cu(I) macrocyclic pyridine-containing ligand (PcL) complex},
author = {V. Pirovano and A. Caselli and A. Colombo and C. Dragonetti and M. Giannangeli and E. Rossi and E. Brambilla},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85090439498&doi=10.1002%2fcctc.202000887&partnerID=40&md5=8ab5342af67e90e02444e8e88686974c},
doi = {10.1002/cctc.202000887},
issn = {18673880},
year = {2020},
date = {2020-01-01},
journal = {ChemCatChem},
volume = {12},
number = {20},
pages = {5250-5255},
publisher = {Wiley Blackwell},
abstract = {A highly reactive and selective catalytic system comprising Cu(I) and a macrocyclic pyridine-containing ligand (Pc−L) for the synthesis of 2-(penta-2,4-dien-1-ylidene) 3-oxoindolines from 4H-furo[3,2-b]indoles and diazoalkane is reported herein. The reaction sequence involves the initial formation of a copper-carbene by Cu(I)-catalyzed decomposition of a diazoalkane followed by copper-carbene to furoindole addition and successive furan ring-opening affording the final products. The reaction proved to be quite general, tolerating EWG as well as EDG substituents on the indole scaffold as well as acceptor or donor/acceptor carbene precursors and products were obtained in good to excellent yields. The proposed methodology allows to overcome some selectivity issues encountered performing similar transformations in the presence of gold(I)-carbenes. Interestingly, two of the 2-alkenylidene-3-oxoindolines are characterized by a second-order nonlinear optical response higher than that of Disperse Red One. © 2020 Wiley-VCH GmbH},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Garanzini, D.; Pirovano, V.; Menghi, I.; Celentano, G.; Rizzato, S.; Rossi, E.; Caselli, A.; Abbiati, G.
[Ag(PcL)]-Catalysed Domino Approach to 6-Substituted Benzoxazino Isoquinolines Journal Article
In: European Journal of Organic Chemistry, vol. 2020, no. 24, pp. 3660-3670, 2020, ISSN: 1434193X.
@article{Garanzini20203660,
title = {[Ag(PcL)]-Catalysed Domino Approach to 6-Substituted Benzoxazino Isoquinolines},
author = {D. Garanzini and V. Pirovano and I. Menghi and G. Celentano and S. Rizzato and E. Rossi and A. Caselli and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85086018996&doi=10.1002%2fejoc.202000341&partnerID=40&md5=90a847db2885be9c00f8817c68cbbd0d},
doi = {10.1002/ejoc.202000341},
issn = {1434193X},
year = {2020},
date = {2020-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2020},
number = {24},
pages = {3660-3670},
publisher = {Wiley-VCH Verlag},
abstract = {In this paper, we describe a new silver catalysed domino approach to 6-substituted benzoxazino isoquinolines starting from 2-alkynylbenzaldehydes and 1-substituted-(2-aminophenyl)methanols. The strategy is characterized by good reaction yields, and can be performed at room temperature as well as under heating (conventional or dielectric) in different reaction times. Best results have been obtained by using silver complexes of macrocyclic pyridine-containing ligands (PcL) as catalysts. The stereoselectivity of the transformation has been investigated by using chiral reaction partners and chiral catalysts, but unfortunately, modest stereoselectivities have been achieved. On the other hand, this approach represents an alternative synthetic strategy for the preparation of 6-substituted benzoxazino isoquinolines, which are the key scaffold of some compounds endowed of biological activity. © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Pirovano, V.; Hamdan, G.; Garanzini, D.; Brambilla, E.; Rossi, E.; Caselli, A.; Abbiati, G.
[Ag(PcL)]-Catalyzed Domino Reactions of 2-Alkynylbenzaldehydes with Electron-Poor Anilines: Synthesis of 1-Aminoisochromenes Journal Article
In: European Journal of Organic Chemistry, vol. 2020, no. 17, pp. 2592-2599, 2020, ISSN: 1434193X.
@article{Pirovano20202592,
title = {[Ag(PcL)]-Catalyzed Domino Reactions of 2-Alkynylbenzaldehydes with Electron-Poor Anilines: Synthesis of 1-Aminoisochromenes},
author = {V. Pirovano and G. Hamdan and D. Garanzini and E. Brambilla and E. Rossi and A. Caselli and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85083809519&doi=10.1002%2fejoc.202000275&partnerID=40&md5=e9e4a4bc9981f73e8b56b3b409e0adef},
doi = {10.1002/ejoc.202000275},
issn = {1434193X},
year = {2020},
date = {2020-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2020},
number = {17},
pages = {2592-2599},
publisher = {Wiley-VCH Verlag},
abstract = {In this paper, we describe the synthesis of neglected 1-aminoisochromene derivatives starting from 2-alkynylbenzaldehydes and electron-poor anilines. The domino reaction is catalyzed by original [AgIPcL] complexes and occurs with complete regioselectivity under mild conditions. The approach well-tolerates different aryl, heteroaryl, alkyl and cycloalkyl substituents on alkyne terminus to give the desired products in modest to very good yields. © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2019
Tseberlidis, G.; Demonti, L.; Pirovano, V.; Scavini, M.; Cappelli, S.; Rizzato, S.; Vicente, R.; Caselli, A.
In: ChemCatChem, vol. 11, no. 19, pp. 4907-4915, 2019, ISSN: 18673880.
@article{Tseberlidis20194907,
title = {Controlling Selectivity in Alkene Oxidation: Anion Driven Epoxidation or Dihydroxylation Catalysed by [Iron(III)(Pyridine-Containing Ligand)] Complexes},
author = {G. Tseberlidis and L. Demonti and V. Pirovano and M. Scavini and S. Cappelli and S. Rizzato and R. Vicente and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071320859&doi=10.1002%2fcctc.201901045&partnerID=40&md5=fb91d56cbd554bb73011bf84fea181b6},
doi = {10.1002/cctc.201901045},
issn = {18673880},
year = {2019},
date = {2019-01-01},
journal = {ChemCatChem},
volume = {11},
number = {19},
pages = {4907-4915},
publisher = {Wiley Blackwell},
abstract = {A highly reactive and selective catalytic system comprising Fe(III) and macrocyclic pyridine-containing ligands (Pc-L) for alkene oxidation by using hydrogen peroxide is reported herein. Four new stable iron(III) complexes have been isolated and characterized. Importantly, depending on the anion of the iron(III) metal complex employed as catalyst, a completely reversed selectivity was observed. When X=OTf, a selective dihydroxylation reaction took place. On the other hand, employing X=Cl resulted in the epoxide as the major product. The reaction proved to be quite general, tolerating aromatic and aliphatic alkenes as well as internal or terminal double bonds and both epoxides and diol products were obtained in good yields with good to excellent selectivities (up to 93 % isolated yield and d.r.=99 : 1). The catalytic system proved its robustness by performing several catalytic cycles, without observing catalyst deactivation. The use of acetone as a solvent and hydrogen peroxide as terminal oxidant renders this catalytic system appealing. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Porta, C. A. M. La; Lionetti, M. C.; Bonfanti, S.; Milan, S.; Ferrario, C.; Rayneau-Kirkhope, D.; Beretta, M.; Hanifpour, M.; Fascio, U.; Ascagni, M.; Paola, L. De; Budrikis, Z.; Schiavoni, M.; Falletta, E.; Caselli, A.; Chepizhko, O.; Tuissi, A.; Vailati, A.; Zapperi, S.
Metamaterial architecture from a self-shaping carnivorous plant Journal Article
In: Proceedings of the National Academy of Sciences of the United States of America, vol. 116, no. 38, pp. 18777-18782, 2019, ISSN: 00278424.
@article{LaPorta201918777,
title = {Metamaterial architecture from a self-shaping carnivorous plant},
author = {C. A. M. La Porta and M. C. Lionetti and S. Bonfanti and S. Milan and C. Ferrario and D. Rayneau-Kirkhope and M. Beretta and M. Hanifpour and U. Fascio and M. Ascagni and L. De Paola and Z. Budrikis and M. Schiavoni and E. Falletta and A. Caselli and O. Chepizhko and A. Tuissi and A. Vailati and S. Zapperi},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85072270264&doi=10.1073%2fpnas.1904984116&partnerID=40&md5=dbbe89d4790d39224b82d94494cd19b5},
doi = {10.1073/pnas.1904984116},
issn = {00278424},
year = {2019},
date = {2019-01-01},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
volume = {116},
number = {38},
pages = {18777-18782},
publisher = {National Academy of Sciences},
abstract = {As meticulously observed and recorded by Darwin, the leaves of the carnivorous plant Drosera capensis L. slowly fold around insects trapped on their sticky surface in order to ensure their digestion. While the biochemical signaling driving leaf closure has been associated with plant growth hormones, how mechanical forces actuate the process is still unknown. Here, we combine experimental tests of leaf mechanics with quantitative measurements of the leaf microstructure and biochemistry to demonstrate that the closure mechanism is programmed into the cellular architecture of D. capensis leaves, which converts a homogeneous biochemical signal into an asymmetric response. Inspired by the leaf closure mechanism, we devise and test a mechanical metamaterial, which curls under homogeneous mechanical stimuli. This kind of metamaterial could find possible applications as a component in soft robotics and provides an example of bioinspired design. © 2019 National Academy of Sciences. All rights reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Brambilla, E.; Pirovano, V.; Giannangeli, M.; Abbiati, G.; Caselli, A.; Rossi, E.
Gold-catalyzed cascade reactions of 4: H -furo[3,2- b] indoles with propargyl esters: Synthesis of 2-alkenylidene-3-oxoindolines Journal Article
In: Organic Chemistry Frontiers, vol. 6, no. 17, pp. 3078-3084, 2019, ISSN: 20524110.
@article{Brambilla20193078,
title = {Gold-catalyzed cascade reactions of 4: H -furo[3,2- b] indoles with propargyl esters: Synthesis of 2-alkenylidene-3-oxoindolines},
author = {E. Brambilla and V. Pirovano and M. Giannangeli and G. Abbiati and A. Caselli and E. Rossi},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071164726&doi=10.1039%2fc9qo00647h&partnerID=40&md5=3008b4bf1217b5d047b17bba2f0b4018},
doi = {10.1039/c9qo00647h},
issn = {20524110},
year = {2019},
date = {2019-01-01},
journal = {Organic Chemistry Frontiers},
volume = {6},
number = {17},
pages = {3078-3084},
publisher = {Royal Society of Chemistry},
abstract = {2-Alkenyliden-indolin-3-ones were synthesised in high yields via a cascade reaction between 4H-furo[3,2-b]indoles and propargyl esters. The cascade sequence involves the initial formation of a gold-carbene species via cationic gold(i) catalysed 1,2-acyloxy migration of properly substituted propargyl esters followed by the addition of gold-carbene to furoindole and successive furan ring-opening affording the final products. The obtained compounds contain an extended π-system linked at the C2 of the indolin-3-ones; they show intense colouration (from yellow to purple) and are characterised by UV measurements. © the Partner Organisations 2019.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Curti, F.; Tiecco, M.; Pirovano, V.; Germani, R.; Caselli, A.; Rossi, E.; Abbiati, G.
In: European Journal of Organic Chemistry, vol. 2019, no. 9, pp. 1904-1914, 2019, ISSN: 1434193X.
@article{Curti20191904,
title = {p-TSA-Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2-Alkynyl-(hetero)-arylcarboxylates: an Alternative Access to 6-Substituted 3,4-Fused 2-Pyranones},
author = {F. Curti and M. Tiecco and V. Pirovano and R. Germani and A. Caselli and E. Rossi and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85061941089&doi=10.1002%2fejoc.201801884&partnerID=40&md5=940919fca36efa08619f292beacda221},
doi = {10.1002/ejoc.201801884},
issn = {1434193X},
year = {2019},
date = {2019-01-01},
journal = {European Journal of Organic Chemistry},
volume = {2019},
number = {9},
pages = {1904-1914},
publisher = {Wiley-VCH Verlag},
abstract = {In this paper, we describe the use of p-TSA based Deep Eutectic Solvents (DESs) as alternative environmental-friendly “active” solvents for the microwave-mediated synthesis of 6-substituted 3,4-fused 2-pyranones, and in particular isocoumarins, starting from 2-alkynyl-(hetero)arylcarboxylates. When the alkyne terminus bears a neutral or an electron-donating group (EDG), the reactions are fast, clean and highly regioselective, to give the 6-endo-dig cyclization products in good to excellent yields. For substrates bearing an electron-withdrawing group (EWG) on the alkyne end, the regioselectivity can be tuned by adding a small amount of silver(I) triflate as co-catalyst. DES was demonstrated to be reusable without loss of efficiency in terms of reaction yields. Based on experimental evidence and previous findings, two competitive mechanisms working simultaneously are proposed to explain the outcomes and the regioselectivity issues. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2018
Carminati, D.; Gallo, E.; Damiano, C.; Caselli, A.; Intrieri, D.
Ruthenium Porphyrin Catalyzed Synthesis of Oxazolidin-2-ones by Cycloaddition of CO2 to Aziridines Journal Article
In: European Journal of Inorganic Chemistry, vol. 2018, no. 48, pp. 5258-5262, 2018, ISSN: 14341948.
@article{Carminati20185258,
title = {Ruthenium Porphyrin Catalyzed Synthesis of Oxazolidin-2-ones by Cycloaddition of CO2 to Aziridines},
author = {D. Carminati and E. Gallo and C. Damiano and A. Caselli and D. Intrieri},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85059249432&doi=10.1002%2fejic.201801208&partnerID=40&md5=5314e087723600123b1d33cacb5b5a24},
doi = {10.1002/ejic.201801208},
issn = {14341948},
year = {2018},
date = {2018-01-01},
journal = {European Journal of Inorganic Chemistry},
volume = {2018},
number = {48},
pages = {5258-5262},
publisher = {Wiley-VCH Verlag},
abstract = {The reaction between N-substituted-2-arylaziridines and CO2 is efficiently promoted by ruthenium(VI) imidoporphyrin complexes and yields a mixture of 5-aryl (A) and 4-aryl (B) substituted oxazolidin-2-ones with a regioisomeric A/B ratio up to 99:1. Several oxazolidin-2-one molecules were synthesized at 100 °C and 0.6 MPa of carbon dioxide by using the low catalytic loading of 1 mol-%. The formation of a deactivated compound, deriving from the ruthenium catalyst, suggested a possible catalytic role of imido nitrogen atoms. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Gargani, E.; Simoni, S.; Benvenuti, C.; Frosinini, R.; Barzanti, G. P.; Roversi, P. F.; Caselli, A.; Guidotti, M.
In: Redia, vol. 101, pp. 201-205, 2018, ISSN: 03704327.
@article{Gargani2018201,
title = {Aclees Cf. Sp. Foveatus (Coleoptera Curculionidae), an exotic pest of ficus carica in Italy: A sustainable approach to defence based on aluminosilicate minerals as host plant masking solids},
author = {E. Gargani and S. Simoni and C. Benvenuti and R. Frosinini and G. P. Barzanti and P. F. Roversi and A. Caselli and M. Guidotti},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85059888830&doi=10.19263%2fREDIA-101.18.28&partnerID=40&md5=0128876d98ef367cb522dcc0d2c3d595},
doi = {10.19263/REDIA-101.18.28},
issn = {03704327},
year = {2018},
date = {2018-01-01},
journal = {Redia},
volume = {101},
pages = {201-205},
publisher = {CREA-DC, Research Centre for Plant Protection and Certification},
abstract = {The exceptionally frequent entries of alien pest are a major source of concern for the farmers who have to protect their crops from unknown insects, often without natural enemies in the new areas. A new pest belonging to the Molytinae family (Coleoptera: Curculionidae), tribe Hylobiini, reported as Aclees sp. cf. foveatus Voss, was recently introduced in Italy. The species is responsible for severe damages in many Italian fig nurseries and orchards, particularly in the Italian Central Northern regions, i.e. Tuscany, Ligury and Latium. Currently, no active ingredients are registered against this insect on fig crops. An innovative and eco-friendly approach for controlling this exotic weevil infestation was investigated, by using montmorillonite-based clays, either in their native state or containing copper(II) species, and clinoptilolite zeolites, in order to check the perception of the adults’ weevil towards the different solid materials and, subsequently, to evaluate the capability of these innovative products to act as masking agent with respect to the host plant and/or as repellent upon contact. The formulations containing copper(II)-exchanged clay and clinoptilolite zeolite showed preliminary promising results in terms of efficacy and environmental sustainability. © 2018 CREA-DC, Research Centre for Plant Protection and Certification. All Rights Reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2017
Tseberlidis, G.; Intrieri, D.; Caselli, A.
Catalytic Applications of Pyridine-Containing Macrocyclic Complexes Journal Article
In: European Journal of Inorganic Chemistry, vol. 2017, no. 30, pp. 3589-3603, 2017, ISSN: 14341948.
@article{Tseberlidis20173589,
title = {Catalytic Applications of Pyridine-Containing Macrocyclic Complexes},
author = {G. Tseberlidis and D. Intrieri and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85027589640&doi=10.1002%2fejic.201700633&partnerID=40&md5=7fa4dd14378175867b3d2bf7ac8c0e71},
doi = {10.1002/ejic.201700633},
issn = {14341948},
year = {2017},
date = {2017-01-01},
journal = {European Journal of Inorganic Chemistry},
volume = {2017},
number = {30},
pages = {3589-3603},
publisher = {Wiley-VCH Verlag},
abstract = {The introduction of a pyridine moiety into the skeleton of a polyazamacrocyclic ligand affects both the thermodynamic properties and the coordination kinetics of the resulting metal complexes. These features have attracted great interest from the scientific community in recent years. The field of application of pyridine-containing macrocyclic ligands ranges from biology to supramolecular chemistry, encompassing MRI, molecular recognition, materials and catalysis. In this microreview we provide a perspective of the catalytic applications of metal complexes of pyridine-containing macrocycles, including an account of investigations from the authors' laboratories dealing with stereoselective C–C and C–O bond-forming reactions. The increased conformational rigidity imposed by the pyridine ring allowed for the isolation and characterisation of metal complexes in high oxidation states and the study of their relevance in oxidation reactions. On the other hand, the very different conformations accessible upon the metal coordination and the easily tuneable synthesis of the macrocyclic ligands have been exploited in stereoselective synthesis. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Tseberlidis, G.; Caselli, A.; Vicente, R.
Carbene X[sbnd]H bond insertions catalyzed by copper(I) macrocyclic pyridine-containing ligand (PcL) complexes Journal Article
In: Journal of Organometallic Chemistry, vol. 835, pp. 1-5, 2017, ISSN: 0022328X.
@article{Tseberlidis20171,
title = {Carbene X[sbnd]H bond insertions catalyzed by copper(I) macrocyclic pyridine-containing ligand (PcL) complexes},
author = {G. Tseberlidis and A. Caselli and R. Vicente},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-85013481378&doi=10.1016%2fj.jorganchem.2017.02.027&partnerID=40&md5=a2552c15a8061cc77c57045bb5495f99},
doi = {10.1016/j.jorganchem.2017.02.027},
issn = {0022328X},
year = {2017},
date = {2017-01-01},
journal = {Journal of Organometallic Chemistry},
volume = {835},
pages = {1-5},
publisher = {Elsevier B.V.},
abstract = {A catalytic system comprising copper(I) and macrocyclic pyridine-containing ligands (Pc-L) proves capable of promoting carbene Si[sbnd]H bond insertions using diazo compounds as the carbene source. This catalytic system showed broad scope and a remarkable robustness as indicated by high TON numbers (up to 30000). Moreover, the use of enynones as carbene sources proved also feasible in hydrosilane insertion using this catalytic system. Finally, the insertion in O[sbnd]H and N[sbnd]H bonds of phenols and anilines, respectively, has been also demonstrated. © 2017 Elsevier B.V.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2016
Carminati, D. M.; Intrieri, D.; Caselli, A.; Gac, S. Le; Boitrel, B.; Toma, L.; Legnani, L.; Gallo, E.
Designing ‘Totem’ C2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations Journal Article
In: Chemistry - A European Journal, vol. 22, no. 38, pp. 13599-13612, 2016, ISSN: 09476539.
@article{Carminati201613599,
title = {Designing ‘Totem’ C2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations},
author = {D. M. Carminati and D. Intrieri and A. Caselli and S. Le Gac and B. Boitrel and L. Toma and L. Legnani and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84983453895&doi=10.1002%2fchem.201602289&partnerID=40&md5=2a3e5d41c7256b55dfc7786475553348},
doi = {10.1002/chem.201602289},
issn = {09476539},
year = {2016},
date = {2016-01-01},
journal = {Chemistry - A European Journal},
volume = {22},
number = {38},
pages = {13599-13612},
publisher = {Wiley-VCH Verlag},
abstract = {The catalytic activity of the iron(III) C2chiral porphyrin Fe(2)(OMe) in alkene cyclopropanation is herein reported. The catalyst promoted the reaction of differently substituted styrenes with diazo derivatives with trans-diastereoselectivities and enantioselectivities up to 99:1 and 87 %, respectively. In addition, high TON and TOF values (up to 10 000 and 120 000 h−1, respectively) were observed indicating good activity and stability of the catalyst in optimized experimental conditions. The study of the cyclopropanation reaction revealed that the porphyrin skeleton is composed of two ‘totem’ parts which were independently responsible for the observed enantio- and diastereoselectivities. To further our research we also investigated the catalytic role of the methoxy axial ligand coordinated to the iron atom. The molecular structure of Fe(2)(OMe) was optimized by DFT calculations which were also employed to achieve a better understanding of the mechanistic details of the carbene transfer reaction. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Tseberlidis, G.; DellÁcqua, M.; Valcarenghi, D.; Gallo, E.; Rossi, E.; Abbiati, G.; Caselli, A.
Silver comes into play: Henry reaction and domino cycloisomerisation sequence catalysed by [Ag(i)(Pc-L)] complexes Journal Article
In: RSC Advances, vol. 6, no. 99, pp. 97404-97419, 2016, ISSN: 20462069.
@article{Tseberlidis201697404,
title = {Silver comes into play: Henry reaction and domino cycloisomerisation sequence catalysed by [Ag(i)(Pc-L)] complexes},
author = {G. Tseberlidis and M. DellÁcqua and D. Valcarenghi and E. Gallo and E. Rossi and G. Abbiati and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84991765469&doi=10.1039%2fc6ra22231e&partnerID=40&md5=7c5c2315fbce9dac026e488f1c9677f9},
doi = {10.1039/c6ra22231e},
issn = {20462069},
year = {2016},
date = {2016-01-01},
journal = {RSC Advances},
volume = {6},
number = {99},
pages = {97404-97419},
publisher = {Royal Society of Chemistry},
abstract = {We report herein the synthesis of new pyridine-containing macrocyclic ligands (Pc-L) bearing a non-innocent pendant arm, by exploiting both chiral and functional properties of natural amino acids. The obtained macrocyclic ligands were employed to synthesize well-defined cationic silver(i) complexes that were shown to be competent catalysts for the Henry (nitroaldol) reaction. Good to excellent yields and full selectivity in the β-nitroalcohol product were obtained starting from electron-poor aromatic aldehydes or other activated aldehydes such as furfural under mild reaction conditions. The straightforward synthesis of the macrocyclic ligands starting from cheap commercially available starting materials allowed the introduction of a suitable basic functionality into the ligand pendant arm, thus providing a bifunctional catalyst. Based on our previous experience in the [Ag(i)(Pc-L)] catalysed domino addition/cycloisomerisation reaction of o-alkynylbenzaldehydes and nucleophiles, the synthesis of isochromenes coupling the Henry reaction and the cycloisomerisation in a single step was subsequently explored. Although with low selectivity, [Ag(i)(Pc-L)] cationic complexes were able to promote such a cascade reaction and a possible mechanism based on experimental evidence has been proposed. © 2016 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2015
Pedrazzini, T.; Pirovano, P.; DellÁcqua, M.; Ragaini, F.; Illiano, P.; Macchi, P.; Abbiati, G.; Caselli, A.
Organometallic Reactivity of [Silver(I)(Pyridine-Containing Ligand)] Complexes Relevant to Catalysis Journal Article
In: European Journal of Inorganic Chemistry, vol. 2015, no. 30, pp. 5089-5098, 2015, ISSN: 14341948.
@article{Pedrazzini20155089,
title = {Organometallic Reactivity of [Silver(I)(Pyridine-Containing Ligand)] Complexes Relevant to Catalysis},
author = {T. Pedrazzini and P. Pirovano and M. DellÁcqua and F. Ragaini and P. Illiano and P. Macchi and G. Abbiati and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84944885700&doi=10.1002%2fejic.201500771&partnerID=40&md5=aa17063e28bce125c9a22eb62307af22},
doi = {10.1002/ejic.201500771},
issn = {14341948},
year = {2015},
date = {2015-01-01},
journal = {European Journal of Inorganic Chemistry},
volume = {2015},
number = {30},
pages = {5089-5098},
publisher = {Wiley-VCH Verlag},
abstract = {Silver(I) complexes of pyiridine-containing macrocyclic ligands (Pc-L) have already been demonstrated as active catalysts for some domino and multicomponent reactions. Here, we report new chiral [AgI(Pc-L)] cationic complexes that have been synthesized and fully characterized, including structural determination by single-crystal X-ray diffraction. The complexes show a rich coordination chemistry, demonstrating both the σ-philic (alcohol and nitrile coordination) and the π-philic (alkyne coordination) nature of silver. The η2 coordination mode of the naphthyl pendant arm of the ligands on silver has been observed in solution by NMR spectroscopic experiments. 2D NMR spectroscopy revealed the presence of positive cross peaks resulting from rotational processes and the rate of rotation was measured by using 2D exchange spectroscopy (EXSY). Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Tseberlidis, G.; Zardi, P.; Caselli, A.; Cancogni, D.; Fusari, M.; Lay, L.; Gallo, E.
Glycoporphyrin Catalysts for Efficient C-H Bond Aminations by Organic Azides Journal Article
In: Organometallics, vol. 34, no. 15, pp. 3774-3781, 2015, ISSN: 02767333.
@article{Tseberlidis20153774,
title = {Glycoporphyrin Catalysts for Efficient C-H Bond Aminations by Organic Azides},
author = {G. Tseberlidis and P. Zardi and A. Caselli and D. Cancogni and M. Fusari and L. Lay and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84938823349&doi=10.1021%2facs.organomet.5b00436&partnerID=40&md5=741c05fb1f430cc2591940a022b64208},
doi = {10.1021/acs.organomet.5b00436},
issn = {02767333},
year = {2015},
date = {2015-01-01},
journal = {Organometallics},
volume = {34},
number = {15},
pages = {3774-3781},
publisher = {American Chemical Society},
abstract = {We report herein the synthesis of new glycoporphyrin ligands which bear a glucopyranoside derivative on each meso-aryl moiety of the porphyrin skeleton. The saccharide unit is directly conjugated to the porphyrin or a triazole spacer is placed between the carbohydrate and porphyrin ring. The obtained glycoporphyrin ligands were employed to synthesize cobalt(II), ruthenium(II), and iron(III) complexes which were tested as catalysts of C-H bond aminations by organic azides. Two of the synthesized complexes were very efficient in promoting catalytic reactions, and the results achieved indicated that ruthenium and iron complexes show an interesting complementary catalytic activity in several amination reactions. The eco-friendly iron catalyst displayed very good chemical stability in catalyzing the amination reaction for three consecutive runs without losing catalytic activity. (Chemical Equation Presented). © 2015 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Bonetti, A.; Beccalli, E.; Caselli, A.; Clerici, F.; Pellegrino, S.; Gelmi, M. L.
Unusual chemoselective rhII -Catalysed transformations of β-diazocarbonyl piperidine cores Journal Article
In: Chemistry - A European Journal, vol. 21, no. 4, pp. 1692-1703, 2015, ISSN: 09476539.
@article{Bonetti20151692,
title = {Unusual chemoselective rhII -Catalysed transformations of β-diazocarbonyl piperidine cores},
author = {A. Bonetti and E. Beccalli and A. Caselli and F. Clerici and S. Pellegrino and M. L. Gelmi},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84920971384&doi=10.1002%2fchem.201405197&partnerID=40&md5=69b12711759ed296e7e8e85264cc2ece},
doi = {10.1002/chem.201405197},
issn = {09476539},
year = {2015},
date = {2015-01-01},
journal = {Chemistry - A European Journal},
volume = {21},
number = {4},
pages = {1692-1703},
publisher = {Wiley-VCH Verlag},
abstract = {The reactivity of various β-diazocarbonyl piperidine scaffolds, characterised by an increased molecular complexity, was tested with various RhII catalysts. The structure of the starting reagent is of relevance to the synthetic results. An unexpected dimerisation took place, starting from the simple piperidine scaffold, to give the hexahydrotetrazine ring system. Products derived from a nitrogen ylide intermediate or aromatic substitution (1,3,4,5-tetrahydro-2,5-methanobenzo[c]azepine and 1,2,3,3a-tetrahydrocyclopenta-[de]isoquinolin-4(5 H)-one rings, respectively) were obtained from tetrahydroisoquinoline derivatives. The chemoselectivity of the reaction could be controlled by the choice of starting reagent, RhII catalyst and the reaction conditions. Finally, it was found that the azepino heterocycle could coordinate to the catalyst to give new RhII complexes. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2014
Viganó, M.; Ferretti, F.; Caselli, A.; Ragaini, F.; Rossi, M.; Mussini, P.; Macchi, P.
Easy entry into reduced Ar-BIANH2 compounds: A new class of quinone/hydroquinone-type redox-active couples with an easily tunable potential Journal Article
In: Chemistry - A European Journal, vol. 20, no. 44, pp. 14451-14464, 2014, ISSN: 09476539.
@article{Viganó201414451,
title = {Easy entry into reduced Ar-BIANH2 compounds: A new class of quinone/hydroquinone-type redox-active couples with an easily tunable potential},
author = {M. Viganó and F. Ferretti and A. Caselli and F. Ragaini and M. Rossi and P. Mussini and P. Macchi},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84915749791&doi=10.1002%2fchem.201403594&partnerID=40&md5=5c7d9b40739d9b4221fc609ee4e3c803},
doi = {10.1002/chem.201403594},
issn = {09476539},
year = {2014},
date = {2014-01-01},
journal = {Chemistry - A European Journal},
volume = {20},
number = {44},
pages = {14451-14464},
publisher = {Wiley-VCH Verlag},
abstract = {Ar-BIANH2 bearing different substituents on the aryl rings have been synthesized in high yield by reduction of the corresponding bis(aryl)acenaphthenequinonediimine (Ar-BIAN) compounds. The structure of p-CH 3C6H4-BIANH2 in the solid state was determined by X-ray diffraction. An exhaustive voltammetric investigation of the two parallel BIAN and BIANH2 series afforded a first rationalization of the redox properties of these molecules, highlighting their analogies with quinone/hydroquinone systems. Such analogies, in combination with the much more negative reduction potential range of Ar-BIAN compounds with respect to quinones, can afford to extend the range of reduction potentials so far obtainable by the use of quinones. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Zardi, P.; Savoldelli, A.; Carminati, D. M.; Caselli, A.; Ragaini, F.; Gallo, E.
Indoles rather than triazoles from the ruthenium porphyrin-catalyzed reaction of alkynes with aryl azides Journal Article
In: ACS Catalysis, vol. 4, no. 11, pp. 3820-3823, 2014, ISSN: 21555435.
@article{Zardi20143820,
title = {Indoles rather than triazoles from the ruthenium porphyrin-catalyzed reaction of alkynes with aryl azides},
author = {P. Zardi and A. Savoldelli and D. M. Carminati and A. Caselli and F. Ragaini and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84909947558&doi=10.1021%2fcs5012712&partnerID=40&md5=61314d3e87a123ebb310ca8674920b84},
doi = {10.1021/cs5012712},
issn = {21555435},
year = {2014},
date = {2014-01-01},
journal = {ACS Catalysis},
volume = {4},
number = {11},
pages = {3820-3823},
publisher = {American Chemical Society},
abstract = {An unprecedented reactivity of aryl azides toward alkynes is presented herein. The reaction performed well in the presence of 2 mol % of ruthenium porphyrin catalysts and afforded substituted indoles instead of triazoles. The procedure is particularly appealing for the synthesis of C3-functionalized indoles which bear EWG on the fragment coming from the azide. The method allowed the synthesis of 15 derivatives with yields up to 95%, high regioselectivity, and without requiring the time-consuming prefunctionalization of reagents and the addition of oxidants and/or additives. © 2014 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Zardi, P.; Caselli, A.; Gallo, E.
Correction: Organic azides: ‘energetic reagents’ for the intermolecular amination of C–H bonds Journal Article
In: Chemical Communications, vol. 50, no. 80, pp. 11961, 2014, ISSN: 13597345.
@article{Intrieri201411961,
title = {Correction: Organic azides: ‘energetic reagents’ for the intermolecular amination of C–H bonds},
author = {D. Intrieri and P. Zardi and A. Caselli and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84941091038&doi=10.1039%2fc4cc90355b&partnerID=40&md5=5be30493b259a50cfa9db672d44151f8},
doi = {10.1039/c4cc90355b},
issn = {13597345},
year = {2014},
date = {2014-01-01},
journal = {Chemical Communications},
volume = {50},
number = {80},
pages = {11961},
abstract = {Correction for ‘Organic azides: “energetic reagents’ for the intermolecular amination of C–H bonds’ by Daniela Intrieri et al., Chem. Commun., 2014, DOI: 10.1039/c4cc03016h. © 2014 The Partner Organisations.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Zardi, P.; Caselli, A.; Gallo, E.
Organic azides: “Energetic reagents” for the intermolecular amination of C-H bonds Journal Article
In: Chemical Communications, vol. 50, no. 78, pp. 11440-11453, 2014, ISSN: 13597345.
@article{Intrieri201411440,
title = {Organic azides: “Energetic reagents” for the intermolecular amination of C-H bonds},
author = {D. Intrieri and P. Zardi and A. Caselli and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84907793211&doi=10.1039%2fc4cc03016h&partnerID=40&md5=425212027d7ed11e442df6844fc56463},
doi = {10.1039/c4cc03016h},
issn = {13597345},
year = {2014},
date = {2014-01-01},
journal = {Chemical Communications},
volume = {50},
number = {78},
pages = {11440-11453},
abstract = {This feature article provides an overview of the application of organic azides for the intermolecular amination of sp3 and sp2 C-H bonds. The catalytic activity of several metal complexes was reviewed underlining both synthetic and mechanistic aspects of the C-H amination. The majority of the aminated compounds reported in literature have been collected in this paper to provide a compendium of published procedures. In addition, the discussion of involved mechanisms has been included to assist the reader to envisage the future potential of organic azides in the synthesis of aza-derivatives. © Partner Organisations 2014.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Trose, M.; DellÁcqua, M.; Pedrazzini, T.; Pirovano, V.; Gallo, E.; Rossi, E.; Caselli, A.; Abbiati, G.
[Silver(I)(Pyridine-Containing Ligand)] Complexes as unusual catalysts for A3-coupling reactions Journal Article
In: Journal of Organic Chemistry, vol. 79, no. 16, pp. 7311-7320, 2014, ISSN: 00223263.
@article{Trose20147311,
title = {[Silver(I)(Pyridine-Containing Ligand)] Complexes as unusual catalysts for A3-coupling reactions},
author = {M. Trose and M. DellÁcqua and T. Pedrazzini and V. Pirovano and E. Gallo and E. Rossi and A. Caselli and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84906080988&doi=10.1021%2fjo500981r&partnerID=40&md5=c5106ff1fe5ad5e0f872906676568ce6},
doi = {10.1021/jo500981r},
issn = {00223263},
year = {2014},
date = {2014-01-01},
journal = {Journal of Organic Chemistry},
volume = {79},
number = {16},
pages = {7311-7320},
publisher = {American Chemical Society},
abstract = {Two original macrocyclic silver(I)(pyridine-containing ligand) complexes [Ag(I)(Pc-L)] were synthesized and characterized. Their ability to catalyze the coupling among aldehydes, terminal alkynes and amines (A3-coupling) was demonstrated. The reaction could be performed under conventional as well as dielectric heating. The catalysts were effective in both cases, but dielectric heating allowed a lower catalyst loading and reduced ratio among reaction partners in shorter reaction times. The reaction scope was broad, including aryl/alkyl aldehydes, aryl/alkyl acetylenes and secondary aliphatic amines. Some unprecedented propargylamines have been prepared. The new catalytic system was also tested with more challenging coupling partners such as aniline and ketones. © 2014 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Zardi, P.; Caselli, A.; Macchi, P.; Ferretti, F.; Gallo, E.
Synthesis of biologically relevant compounds by ruthenium porphyrin catalyzed amination of benzylic C-H bonds Journal Article
In: Organometallics, vol. 33, no. 9, pp. 2210-2218, 2014, ISSN: 02767333.
@article{Zardi20142210,
title = {Synthesis of biologically relevant compounds by ruthenium porphyrin catalyzed amination of benzylic C-H bonds},
author = {P. Zardi and A. Caselli and P. Macchi and F. Ferretti and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84900428132&doi=10.1021%2fom500064d&partnerID=40&md5=52413f13f89c1b42313d4725cd474c3c},
doi = {10.1021/om500064d},
issn = {02767333},
year = {2014},
date = {2014-01-01},
journal = {Organometallics},
volume = {33},
number = {9},
pages = {2210-2218},
publisher = {American Chemical Society},
abstract = {Herein we report the catalytic activity of ruthenium porphyrin complexes to promote the amination of benzylic C-H bonds by aryl azides, yielding α- and β-amino esters. The catalytic methodology is also effective to synthesize two derivatives of methyl l-3-phenyllactate in order to convert one of them into the corresponding β-lactam. The catalytic experimental conditions have been optimized on the basis of a preliminary mechanistic investigation which underlines the pivotal role of the substrate concentration to maximize the reaction productivity. © 2014 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Dellacqua, M.; Castano, B.; Cecchini, C.; Pedrazzini, T.; Pirovano, V.; Rossi, E.; Caselli, A.; Abbiati, G.
Mild regiospecific synthesis of 1-alkoxy-isochromenes catalyzed by well-defined [silver(I)(pyridine-containing ligand)] complexes Journal Article
In: Journal of Organic Chemistry, vol. 79, no. 8, pp. 3494-3505, 2014, ISSN: 00223263.
@article{Dellacqua20143494,
title = {Mild regiospecific synthesis of 1-alkoxy-isochromenes catalyzed by well-defined [silver(I)(pyridine-containing ligand)] complexes},
author = {M. Dellacqua and B. Castano and C. Cecchini and T. Pedrazzini and V. Pirovano and E. Rossi and A. Caselli and G. Abbiati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84899013234&doi=10.1021%2fjo5002559&partnerID=40&md5=82b507d308fdf6850b47b3a1e8ae2bf4},
doi = {10.1021/jo5002559},
issn = {00223263},
year = {2014},
date = {2014-01-01},
journal = {Journal of Organic Chemistry},
volume = {79},
number = {8},
pages = {3494-3505},
publisher = {American Chemical Society},
abstract = {The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(I) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth 1H NMR experiments and an aimed trapping experiment. © 2014 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Gac, S. L.; Caselli, A.; Rose, E.; Boitrel, B.; Gallo, E.
Highly diastereoselective cyclopropanation of α-methylstyrene catalysed by a C 2-symmetrical chiral iron porphyrin complex Journal Article
In: Chemical Communications, vol. 50, no. 15, pp. 1811-1813, 2014, ISSN: 13597345.
@article{Intrieri20141811,
title = {Highly diastereoselective cyclopropanation of α-methylstyrene catalysed by a C 2-symmetrical chiral iron porphyrin complex},
author = {D. Intrieri and S. L. Gac and A. Caselli and E. Rose and B. Boitrel and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84893073939&doi=10.1039%2fc3cc48605b&partnerID=40&md5=71f74439c14e4f80a5b9eda5e308eb8e},
doi = {10.1039/c3cc48605b},
issn = {13597345},
year = {2014},
date = {2014-01-01},
journal = {Chemical Communications},
volume = {50},
number = {15},
pages = {1811-1813},
abstract = {A new chiral iron porphyrin-based catalyst performed α-methylstyrene stereoselective cyclopropanation with excellent yields (up to 99%), enantio- and diastereoselectivities (ee trans up to 87%, trans/cis ratios up to 99 : 1) and outstanding TON and TOF values (up to 20 000 and 120 000 h−1 respectively). 2014 © The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Castano, B.; Gallo, E.; Cole-Hamilton, D. J.; Santo, V. Dal; Psaro, R.; Caselli, A.
In: Green Chemistry, vol. 16, no. 6, pp. 3202-3209, 2014, ISSN: 14639262.
@article{Castano20143202,
title = {Continuous flow asymmetric cyclopropanation reactions using Cu(i) complexes of Pc-L* ligands supported on silica as catalysts with carbon dioxide as a carrier},
author = {B. Castano and E. Gallo and D. J. Cole-Hamilton and V. Dal Santo and R. Psaro and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84901611436&doi=10.1039%2fc4gc00119b&partnerID=40&md5=aa9fa74086be5b079f5d5190beaff6c5},
doi = {10.1039/c4gc00119b},
issn = {14639262},
year = {2014},
date = {2014-01-01},
journal = {Green Chemistry},
volume = {16},
number = {6},
pages = {3202-3209},
publisher = {Royal Society of Chemistry},
abstract = {Continuous flow heterogeneous asymmetric cyclopropanations catalysed by supported hydrogen-bonded (SHB) chiral copper(i) complexes of pyridine containing tetraazamacrocyclic ligands Pc-L* using CO2 as a transport vector are described. The catalytic system showed high stability and good recyclability without loss of activity for at least 24 h in CO2 and catalyst turnover numbers up to 440 were obtained with excellent conversion (up to 99%) and high selectivity (up to 88%). No leaching of copper was observed. Cyclopropane products from both aromatic and aliphatic olefins were obtained in good yields with enantiomeric excesses up to 72%. This journal is © the Partner Organisations 2014.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2013
Castano, B.; Guidone, S.; Gallo, E.; Ragaini, F.; Casati, N.; MacChi, P.; Sisti, M.; Caselli, A.
Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) Journal Article
In: Dalton Transactions, vol. 42, no. 7, pp. 2451-2462, 2013, ISSN: 14779226.
@article{Castano20132451,
title = {Asymmetric cyclopropanation of olefins catalysed by Cu(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)},
author = {B. Castano and S. Guidone and E. Gallo and F. Ragaini and N. Casati and P. MacChi and M. Sisti and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84872722290&doi=10.1039%2fc2dt32347h&partnerID=40&md5=c51ab1c1b8c379c05dbfe421efe67ef2},
doi = {10.1039/c2dt32347h},
issn = {14779226},
year = {2013},
date = {2013-01-01},
journal = {Dalton Transactions},
volume = {42},
number = {7},
pages = {2451-2462},
abstract = {The synthesis and characterisation of copper(i) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) and their use as catalysts in asymmetric cyclopropanation reactions are reported. All ligands and metal complexes were fully characterised, including crystal structures of some species determined by X-ray diffraction on single crystals. This allowed characterising the very different conformations of the macrocycles which could be induced by different substituents or by metal complexation. The strategy adopted for the ligand synthesis is very flexible allowing several structural modifications. A small library of macrocyclic ligands possessing the same donor properties but with either C1 or C2 symmetry was synthesized. Cyclopropane products with both aromatic and aliphatic olefins were obtained in good yields and enantiomeric excesses up to 99%. © 2013 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Castano, B.; Zardi, P.; Hönemann, Y. C.; Galarneau, A.; Gallo, E.; Psaro, R.; Caselli, A.; Santo, V. D.
Silica "sHB" chiral Pc-L* copper complexes for halogen-free solvent cyclopropanation reactions Journal Article
In: RSC Advances, vol. 3, no. 44, pp. 22199-22205, 2013, ISSN: 20462069.
@article{Castano201322199,
title = {Silica "sHB" chiral Pc-L* copper complexes for halogen-free solvent cyclopropanation reactions},
author = {B. Castano and P. Zardi and Y. C. Hönemann and A. Galarneau and E. Gallo and R. Psaro and A. Caselli and V. D. Santo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84886524564&doi=10.1039%2fc3ra44806a&partnerID=40&md5=d562769afca3ee9dfec4a20f6dc3adcd},
doi = {10.1039/c3ra44806a},
issn = {20462069},
year = {2013},
date = {2013-01-01},
journal = {RSC Advances},
volume = {3},
number = {44},
pages = {22199-22205},
publisher = {Royal Society of Chemistry},
abstract = {The grafting of the preformed Pc-L* (pyridine containing macrocyclic ligands) copper(i) complexes on different ordered and non-ordered silicas, and their use, under heterogeneous batch conditions, as catalysts for the olefin cyclopropanation are reported. High yields (up to 99%) and good recyclability in halogen-free solvent reactions were obtained, together with negligible copper leaching (0.1% of total copper). © The Royal Society of Chemistry 2013.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2012
Zardi, P.; Intrieri, D.; Caselli, A.; Gallo, E.
Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides Journal Article
In: Journal of Organometallic Chemistry, vol. 716, pp. 269-274, 2012, ISSN: 0022328X.
@article{Zardi2012269,
title = {Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides},
author = {P. Zardi and D. Intrieri and A. Caselli and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84865002399&doi=10.1016%2fj.jorganchem.2012.07.013&partnerID=40&md5=32c1d6226eecb875ff9e4d895add9db9},
doi = {10.1016/j.jorganchem.2012.07.013},
issn = {0022328X},
year = {2012},
date = {2012-01-01},
journal = {Journal of Organometallic Chemistry},
volume = {716},
pages = {269-274},
abstract = {Co(porphyrin) complexes promote an unusual reactivity of dihydronaphthalene towards several aryl azides. The reaction affords the benzylic amine of tetrahydronaphthalene instead yielding the amine of dihydronaphthalene as it normally happens in the presence of Ru(porphyrin)CO catalysts. The amination process occurs with the concomitant reduction of the dihydronaphthalene double bond probably due to the high reactivity of the endocyclic CC bond coupled with the good hydrogen donor capability of dihydronaphthalene. Two mechanisms for this reaction are proposed. © 2012 Elsevier B.V. All rights reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Youssef, N. S.; El-Seidy, A. M. A.; Schiavoni, M.; Castano, B.; Ragaini, F.; Gallo, E.; Caselli, A.
Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations Journal Article
In: Journal of Organometallic Chemistry, vol. 714, pp. 94-103, 2012, ISSN: 0022328X.
@article{Youssef201294,
title = {Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations},
author = {N. S. Youssef and A. M. A. El-Seidy and M. Schiavoni and B. Castano and F. Ragaini and E. Gallo and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84863727829&doi=10.1016%2fj.jorganchem.2012.03.018&partnerID=40&md5=e3c26d91aa76bcf89ddb3f3e8890936c},
doi = {10.1016/j.jorganchem.2012.03.018},
issn = {0022328X},
year = {2012},
date = {2012-01-01},
journal = {Journal of Organometallic Chemistry},
volume = {714},
pages = {94-103},
abstract = {New copper complexes of several thiosemicarbazones have been prepared and characterized. All complexes have been prepared by employing Cu (II) acetate hydrate, but analytical and spectroscopical data for the isolated complexes revealed that in most cases a reduction to copper (I) occurred. Cyclopropanation reactions of several olefins by ethyldiazoacetate (EDA) in the presence of catalytic amounts of the complexes were examined. The reported results showed that all complexes are competent catalysts for the cyclopropanation reaction of unactivated olefins. Cyclopropanes were obtained in high yields (up to 97%, TON up to 18,400) with moderate to excellent diastereoselectivities (up to >99%). © 2012 Elsevier B.V. All rights reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Mariani, M.; Caselli, A.; Ragaini, F.; Gallo, E.
[Ru(TPP)CO]-catalysed intramolecular benzylic C-H bond amination, affording phenanthridine and dihydrophenanthridine derivatives Journal Article
In: Chemistry - A European Journal, vol. 18, no. 34, pp. 10487-10490, 2012, ISSN: 09476539.
@article{Intrieri201210487,
title = {[Ru(TPP)CO]-catalysed intramolecular benzylic C-H bond amination, affording phenanthridine and dihydrophenanthridine derivatives},
author = {D. Intrieri and M. Mariani and A. Caselli and F. Ragaini and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84864969921&doi=10.1002%2fchem.201200888&partnerID=40&md5=829b1d551928f6b6c5db607a576b9936},
doi = {10.1002/chem.201200888},
issn = {09476539},
year = {2012},
date = {2012-01-01},
journal = {Chemistry - A European Journal},
volume = {18},
number = {34},
pages = {10487-10490},
abstract = {Shedding light on azides: [Ru(TPP)CO] (TPP=tetraphenyl porphyrin dianion), white light and O2 were found to be a suitable catalyst combination to perform the annulation of several biaryl azides (see scheme). The high chemoselectivity of the process allows the synthesis of phenanthridines and dihydrophenanthridines in good yield and purity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Caselli, A.; Ragaini, F.; MacChi, P.; Casati, N.; Gallo, E.
Insights into the mechanism of the ruthenium-porphyrin-catalysed allylic amination of olefins by aryl azides Journal Article
In: European Journal of Inorganic Chemistry, no. 3, pp. 569-580, 2012, ISSN: 14341948.
@article{Intrieri2012569,
title = {Insights into the mechanism of the ruthenium-porphyrin-catalysed allylic amination of olefins by aryl azides},
author = {D. Intrieri and A. Caselli and F. Ragaini and P. MacChi and N. Casati and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84856053740&doi=10.1002%2fejic.201100763&partnerID=40&md5=af74d26920adece8f13f7c2daa36e67d},
doi = {10.1002/ejic.201100763},
issn = {14341948},
year = {2012},
date = {2012-01-01},
journal = {European Journal of Inorganic Chemistry},
number = {3},
pages = {569-580},
abstract = {This paper describes the synthesis of allylic amines by aryl azides (ArN 3) catalysed by [Ru(TPP)CO] (TPP = dianion of tetraphenylporphyrin). The employment of aryl azides renders the methodology sustainable as the formation of molecular nitrogen is the only stoichiometric byproduct. The isolation of catalytic intermediates and spectroscopic and kinetic studies revealed interesting information about the reaction mechanism, which could improve its catalytic efficiency in future research. An important result is the X-ray characterisation of [Ru(TPP)(ArN) 2] [Ar = 3,5-(CF 3) 2C 6H 3], which is active in both stoichiometric and catalytic nitrene transfer reactions. The proposed involvement of carbonyl-monoimido-ruthenium porphyrin complexes in the catalytic cycle is also derived from our kinetic and experimental results. All the data indicate the coexistence of two mechanisms, where the electronic nature of the engaged aryl azide and olefin concentration determine one mechanism or the other. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2011
Castano, B.; Pedrazzini, T.; Sisti, M.; Gallo, E.; Ragaini, F.; Casati, N.; Caselli, A.
Henry reaction catalyzed by copper(I) complexes of a new pyridine-containing macrocyclic ligand Journal Article
In: Applied Organometallic Chemistry, vol. 25, no. 11, pp. 824-829, 2011, ISSN: 02682605.
@article{Castano2011824,
title = {Henry reaction catalyzed by copper(I) complexes of a new pyridine-containing macrocyclic ligand},
author = {B. Castano and T. Pedrazzini and M. Sisti and E. Gallo and F. Ragaini and N. Casati and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84155171120&doi=10.1002%2faoc.1846&partnerID=40&md5=adb39e87590e45a40b8e9472568c8e7d},
doi = {10.1002/aoc.1846},
issn = {02682605},
year = {2011},
date = {2011-01-01},
journal = {Applied Organometallic Chemistry},
volume = {25},
number = {11},
pages = {824-829},
abstract = {The synthesis and characterization of copper(I) complexes of the novel pyridine-containing macrocyclic ligand (PC-L) and their use as catalysts in the Henry reaction are reported. The pyridine-based 12-membered tetraaza macrocyclic (PC-L) ligand 1 can be obtained in good overall yield (85%) from commercially available starting materials. The Cu(I) complexes showed good catalytic activities in the Henry reaction of different aldehydes and nitroalkanes. Remarkable diastereoselectivity was observed when isatine was reacted with nitroethane under catalytic conditions. Copyright © 2011 John Wiley & Sons, Ltd.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Intrieri, D.; Caselli, A.; Gallo, E.
Cyclopropanation reactions mediated by group 9 metal porphyrin complexes Journal Article
In: European Journal of Inorganic Chemistry, no. 33, pp. 5071-5081, 2011, ISSN: 14341948.
@article{Intrieri20115071,
title = {Cyclopropanation reactions mediated by group 9 metal porphyrin complexes},
author = {D. Intrieri and A. Caselli and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-81255203764&doi=10.1002%2fejic.201100664&partnerID=40&md5=7cf361b76a03847e1d9d9e995a5a5ade},
doi = {10.1002/ejic.201100664},
issn = {14341948},
year = {2011},
date = {2011-01-01},
journal = {European Journal of Inorganic Chemistry},
number = {33},
pages = {5071-5081},
abstract = {The one-pot reaction of diazo compounds with olefins represents a useful strategy to synthesise cyclopropanes, which are important both as starting materials for the synthesis of organic compounds and because of their intrinsic pharmaceutical properties. Herein we describe the catalytic activity of group 9 metal porphyrin complexes to cyclopropanate olefins that present different electronic behaviour. All the most important porphyrin-based methodologies have been reviewed, stressing the stereocontrol of the reactions achieved in each case. Moreover, mechanism investigations have provided data that can help greatly to elaborate more efficient catalytic systems in the future. The reaction of diazo derivatives with olefins represents a valid tool to synthesise cyclopropanes. Rhodium and cobalt porphyrin complexes have been extensively employed as catalysts, and in several cases outstanding stereocontrol has been achieved. Recent advances in understanding the reaction mechanism will be crucial to plan new and more efficient catalytic systems. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Cenini, S.; Ragaini, F.; Gallo, E.; Caselli, A.
Synthesis of heterocycles by intramolecular cyclization of organic Azides Journal Article
In: Current Organic Chemistry, vol. 15, no. 10, pp. 1578-1592, 2011, ISSN: 13852728.
@article{Cenini20111578,
title = {Synthesis of heterocycles by intramolecular cyclization of organic Azides},
author = {S. Cenini and F. Ragaini and E. Gallo and A. Caselli},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-79954991052&doi=10.2174%2f138527211795378164&partnerID=40&md5=4d4816c6c220500c48454bebb329707e},
doi = {10.2174/138527211795378164},
issn = {13852728},
year = {2011},
date = {2011-01-01},
journal = {Current Organic Chemistry},
volume = {15},
number = {10},
pages = {1578-1592},
abstract = {A review of synthetic methodologies reported in the last five years that yield N-heterocyclic products by intramolecular cyclization of organic azides with a particular emphasis on transformations catalyzed by metal complexes is presented. These reactions have been classified according to the ring size of the formed heterocycle.© 2011 Bentham Science Publishers Ltd.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Ragaini, F.; Larici, H.; Rimoldi, M.; Caselli, A.; Ferretti, F.; MacChi, P.; Casati, N.
Mapping palladium reduction by carbon monoxide in a catalytically relevant system. a novel palladium(I) dimer Journal Article
In: Organometallics, vol. 30, no. 8, pp. 2385-2393, 2011, ISSN: 02767333.
@article{Ragaini20112385,
title = {Mapping palladium reduction by carbon monoxide in a catalytically relevant system. a novel palladium(I) dimer},
author = {F. Ragaini and H. Larici and M. Rimoldi and A. Caselli and F. Ferretti and P. MacChi and N. Casati},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-79954509047&doi=10.1021%2fom200118v&partnerID=40&md5=3f0865c7a727b52f470596e28305141c},
doi = {10.1021/om200118v},
issn = {02767333},
year = {2011},
date = {2011-01-01},
journal = {Organometallics},
volume = {30},
number = {8},
pages = {2385-2393},
abstract = {Reaction of neutral palladium(II) complexes with chelating nitrogen ligands of the phenanthroline family had been earlier found to proceed through the formation of a CO adduct, which is then reduced to another observable complex before decomposing to metallic palladium. We have now extended this study and completely characterized by single-crystal X-ray diffraction one member of this class of compounds. The intermediate is an unprecedented type of palladium(I) dimer with two bridging COs. The same complex could also be obtained by a conproportionation reaction of a Pd0 with a PdII complex. The picture of the reactivity of neutral palladium(II) complexes with phenanthroline ligands in a CO atmosphere was completed by the identification of two byproducts of the main reaction. © 2011 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
2010
Boldini, I.; Guillemot, G.; Caselli, A.; Proust, A.; Gallo, E.
Polyoxometalates: Powerful catalysts for atom-efficient cyclopropanations Journal Article
In: Advanced Synthesis and Catalysis, vol. 352, no. 14-15, pp. 2365-2370, 2010, ISSN: 16154150.
@article{Boldini20102365,
title = {Polyoxometalates: Powerful catalysts for atom-efficient cyclopropanations},
author = {I. Boldini and G. Guillemot and A. Caselli and A. Proust and E. Gallo},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-78349243220&doi=10.1002%2fadsc.201000378&partnerID=40&md5=23577edf8b8a07fc93b558ab10c75897},
doi = {10.1002/adsc.201000378},
issn = {16154150},
year = {2010},
date = {2010-01-01},
journal = {Advanced Synthesis and Catalysis},
volume = {352},
number = {14-15},
pages = {2365-2370},
abstract = {The polyoxometalate-based catalytic cyclopropanation of olefins by ethyl diazoacetate (EDA) is reported. The outstanding catalyst productivity (TONs up to 100,000) and the use of equimolar EDA/olefin ratio confer to the methodology a high sustainability. Preliminary mechanistic investigations are also discussed. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}