The cost-effective TPPH2/TBACl-catalyzed (TPPH2=dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N-aryl aziridines was successful in synthesizing N-aryl oxazolidin-2-ones. A catalytic tandem reaction was also developed, in which N-aryl aziridines were initially synthesized and then reacted with carbon dioxide without being purified. The procedure occurred with a very high atom economy, molecular nitrogen being the only by-product of the entire tandem process. In addition, the mechanism of catalytic cycle was investigated by DFT calculations. (Figure presented.).

A Metal-Free Synthesis of N-Aryl Oxazolidin-2-Ones by the One-Pot Reaction of Carbon Dioxide with N-Aryl Aziridines / P. Sonzini, C. Damiano, D. Intrieri, G. Manca, E. Gallo. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - (2020). [Epub ahead of print] [10.1002/adsc.202000175]

A Metal-Free Synthesis of N-Aryl Oxazolidin-2-Ones by the One-Pot Reaction of Carbon Dioxide with N-Aryl Aziridines

P. Sonzini
Primo
;
C. Damiano
Secondo
;
D. Intrieri;E. Gallo
Ultimo
2020

Abstract

The cost-effective TPPH2/TBACl-catalyzed (TPPH2=dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N-aryl aziridines was successful in synthesizing N-aryl oxazolidin-2-ones. A catalytic tandem reaction was also developed, in which N-aryl aziridines were initially synthesized and then reacted with carbon dioxide without being purified. The procedure occurred with a very high atom economy, molecular nitrogen being the only by-product of the entire tandem process. In addition, the mechanism of catalytic cycle was investigated by DFT calculations. (Figure presented.).
Aziridine; Carbon dioxide; DFT study; N-aryl oxazolidin-2-one; Porphyrin
Settore CHIM/03 - Chimica Generale e Inorganica
   Piano Sviluppo Unimi - Programma Transition Grant - Horizon 2020 - Linea 1B. Progetto "Italia per l'Europa"
2020
giu-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/749169
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