Nicola Panza
ORCID: https://orcid.org/0000-0002-9627-9741
Dr. Nicola Panza was born in Bergamo, Italy in 1994. He received his master’s degree in chemical sciences in 2019 at the University of Milan, with a thesis focused on oxidative catalytic methods using iron complexes of pyclen ligands. He is currently a PhD fellow in Industrial Chemistry under the supervision of prof Caselli and he is working on the development of innovative simple catalytic systems for the valorization of waste materials. The main research activity focus on the transformation of CO₂ into added value products such as cyclic organic carbonates or oxazolidinones, and his main research interest lies in the field of organic chemistry, coordination chemistry, homogeneous catalysis and sustainable chemistry.
Publications
2024
10.
Alberti, Matteo; Gianelli, Marta; Panza, Nicola; Zákutná, Dominika; Matulková, Irena; Caselli, Alessandro
In: European Journal of Inorganic Chemistry, vol. 27, no. 36, pp. e202400494, 2024.
@article{nokey,
title = {Iron and Zinc Metallates Supported on Ion Exchange Resins: Synergistic Catalysts for the Solvent-Free Cyclic Carbonate Synthesis from Epoxides and CO₂},
author = {Matteo Alberti and Marta Gianelli and Nicola Panza and Dominika Zákutná and Irena Matulková and Alessandro Caselli},
doi = {10.1002/ejic.202400494},
year = {2024},
date = {2024-12-24},
urldate = {2024-12-24},
journal = {European Journal of Inorganic Chemistry},
volume = {27},
number = {36},
pages = {e202400494},
abstract = {Despite extensive research into developing efficient and environmentally friendly catalysts for converting CO2 over the last decade, the search for a robust and cost-effective catalytic system is ongoing. This study describes developing and applying a new catalytic system using inexpensive ferrate and zincate anions immobilized on easily available commercial ion exchange resins (IER) to produce cyclic carbonates from CO2 with high efficiency and low cost. Two polystyrene-based anion exchange resins, AmberlystTM A26-Cl (A26-Cl) and AmberliteTM IRA-400-Cl (IRA400-Cl), were compared. The results demonstrated the catalysts’ remarkable activity under mild conditions and demonstrated the synergistic effect between the polystyrene support and the active ammonium metallates, presenting a scalable, eco-friendly method for cyclic carbonate production using waste CO2. A Design of Experiment (DoE) approach was implemented to optimize the catalytic cycloaddition of CO2. The reaction scale-up to produce a 5 g batch of propylene oxide and conducting recycling tests demonstrated that the catalyst retained its activity over four cycles. The research also explored the use of various epoxides and found that terminal epoxides produced very good yields. In summary, this study introduces a cost-effective, scalable method for converting CO2 into valuable cyclic carbonates, leveraging the synergistic effects of polystyrene supports and active ammonium metallates.},
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Despite extensive research into developing efficient and environmentally friendly catalysts for converting CO2 over the last decade, the search for a robust and cost-effective catalytic system is ongoing. This study describes developing and applying a new catalytic system using inexpensive ferrate and zincate anions immobilized on easily available commercial ion exchange resins (IER) to produce cyclic carbonates from CO2 with high efficiency and low cost. Two polystyrene-based anion exchange resins, AmberlystTM A26-Cl (A26-Cl) and AmberliteTM IRA-400-Cl (IRA400-Cl), were compared. The results demonstrated the catalysts’ remarkable activity under mild conditions and demonstrated the synergistic effect between the polystyrene support and the active ammonium metallates, presenting a scalable, eco-friendly method for cyclic carbonate production using waste CO2. A Design of Experiment (DoE) approach was implemented to optimize the catalytic cycloaddition of CO2. The reaction scale-up to produce a 5 g batch of propylene oxide and conducting recycling tests demonstrated that the catalyst retained its activity over four cycles. The research also explored the use of various epoxides and found that terminal epoxides produced very good yields. In summary, this study introduces a cost-effective, scalable method for converting CO2 into valuable cyclic carbonates, leveraging the synergistic effects of polystyrene supports and active ammonium metallates.
9.
Alberti, Matteo; Dariol, Andrea; Panza, Nicola; Abbiati, Giorgio; Caselli, Alessandro
Ammonium Zincates as Catalysts for the Microwave-Enhanced Synthesis of Symmetric Piperazines by Regioselective Opening of Aziridines Journal Article
In: Chemistry – An Asian Journal, vol. 19, no. 22, pp. e202400688, 2024.
@article{https://doi.org/10.1002/asia.202400688,
title = {Ammonium Zincates as Catalysts for the Microwave-Enhanced Synthesis of Symmetric Piperazines by Regioselective Opening of Aziridines},
author = {Matteo Alberti and Andrea Dariol and Nicola Panza and Giorgio Abbiati and Alessandro Caselli},
url = {https://aces.onlinelibrary.wiley.com/doi/abs/10.1002/asia.202400688},
doi = {https://doi.org/10.1002/asia.202400688},
year = {2024},
date = {2024-01-01},
journal = {Chemistry – An Asian Journal},
volume = {19},
number = {22},
pages = {e202400688},
abstract = {Abstract 2,5-disubstituted N,N’-alkylpiperazines represent an interesting target in organic synthesis both for pharmaceutical or agrochemical applications and as a promising class of ligands in coordination chemistry. We report here a microwave-enhanced synthesis of these compounds starting from non-activated N-alkyl aziridines in the presence of catalytic amounts of simple ammonium metallates. A remarkable TOF of 2787.9 h−1 has been observed in the case of [TBA]2[ZnI4] as the catalyst (catalyst loading 0.1 mol %) and with an almost complete selectivity (up to 97 %) in favor of both diastereoisomers (meso and chiral form) of the target 2,5-disubstituted piperazines, obtained in 1 : 1 ratio. The two isomers are easily separated, because the meso form precipitates in pure from the reaction crude. A stereochemical investigation and the unprecedented isolation of 2,6-disubstituted N,N’-alkylpiperazines allowed us to shed light on the reaction mechanism.},
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Abstract 2,5-disubstituted N,N’-alkylpiperazines represent an interesting target in organic synthesis both for pharmaceutical or agrochemical applications and as a promising class of ligands in coordination chemistry. We report here a microwave-enhanced synthesis of these compounds starting from non-activated N-alkyl aziridines in the presence of catalytic amounts of simple ammonium metallates. A remarkable TOF of 2787.9 h−1 has been observed in the case of [TBA]2[ZnI4] as the catalyst (catalyst loading 0.1 mol %) and with an almost complete selectivity (up to 97 %) in favor of both diastereoisomers (meso and chiral form) of the target 2,5-disubstituted piperazines, obtained in 1 : 1 ratio. The two isomers are easily separated, because the meso form precipitates in pure from the reaction crude. A stereochemical investigation and the unprecedented isolation of 2,6-disubstituted N,N’-alkylpiperazines allowed us to shed light on the reaction mechanism.
2022
8.
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.},
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pubstate = {published},
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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.
7.
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}
}
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.
6.
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}
}
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.
5.
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}
}
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.
4.
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}.},
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We have recently shown that simple ammonium ferrates are competent catalyst for the cycloaddition reaction of CO2 to epoxides under moderate reaction conditions (T = 100°C, P(CO2) = 0.8 MPa). We report here that ammonium zincates of general formulae [TBA]2 [ZnX4] (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 CO2 pressure). Using [TBA]2[ZnBr4] complex as homogeneous catalyst at 100°C and P(CO2) = 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 CO2 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 CO2.
2021
3.
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},
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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
2.
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 = {},
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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
2020
1.
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}
}
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