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.

Ammonium Ferrate‐Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3‐Oxazolidin‐2‐ones / N. Panza, M. Alberti, S. Galiè, C. Damiano, F. Cargnoni, M. Italo Trioni, A. Caselli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2022:40(2022 Oct 25), pp. e202200908.1-e202200908.9. [10.1002/ejoc.202200908]

Ammonium Ferrate‐Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3‐Oxazolidin‐2‐ones

N. Panza
Primo
;
C. Damiano;F. Cargnoni;M. Italo Trioni
Penultimo
;
A. Caselli
Ultimo
2022

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.
Chemical utilization of CO2; Density functional calculations; Homogeneous catalysis; Iron; Oxazolidinones;
Settore CHIM/03 - Chimica Generale e Inorganica
PSRL621PRISO_01 - One Health Action Hub: task force di Ateneo per la resilienza di ecosistemi territoriali (1H_Hub) (Linea Strategica 3, Tema One health, one earth) - RISO, PATRIZIA - PSR_LINEA6_ / Piano di sviluppo di ricerca - Grandi Sfide di Ateneo - Linea 6 - 2021
19-set-2022
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202200908
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/943890
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