Matteo Alberti
Matteo Alberti
Matteo Alberti was born in Milan, Italy in 1998. He received his master’s degree in chemical sciences in 2022 at the University of Milan, with a thesis on the catalytic cycloaddition of carbon dioxide to aziridines and the dimerization of aziridines. He is currently a PhD fellow in Chemistry under the supervision of prof. Caselli and he is working on the development of catalytic systems involving nitrene transfers on olefins to yield aziridines.
Publications
2022
2.
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}
}
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.
1.
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}
}
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.