Thanks to its intrinsic eco-compatibility and high atom economy, the direct insertion of CO2 into three-membered rings, such as epoxides and aziridines, has become one of the most investigated strategies for the synthesis of cyclic carbonates and oxazolidin-2-ones. In this view, the following short account summarizes our recent results regarding the use of ruthenium porphyrin complexes and metal-free porphyrins, in combination with TBACl (tetrabutyl ammonium chloride), to promote the CO2 conversion into cyclic carbonates as well as N-alkyl and N-aryl oxazolidin-2-ones. Experimental data are described in combination with performed DFT studies that allowed proposing a reaction mechanism for the CO2 cycloaddition to aziridines promoted by metal-free porphyrins in which the adduct formed by TPPH2 and TBACl represents the real catalytic active species.

The CO2 cycloaddition to epoxides and aziridines promoted by porphyrin-based catalysts / C. Damiano, P. Sonzini, M. Cavalleri, G. Manca, E. Gallo. - In: INORGANICA CHIMICA ACTA. - ISSN 0020-1693. - 540:(2022 Sep 24), pp. 121065.1-121065.10. [10.1016/j.ica.2022.121065]

The CO2 cycloaddition to epoxides and aziridines promoted by porphyrin-based catalysts

C. Damiano
Primo
;
P. Sonzini
Secondo
;
M. Cavalleri;E. Gallo
Ultimo
2022

Abstract

Thanks to its intrinsic eco-compatibility and high atom economy, the direct insertion of CO2 into three-membered rings, such as epoxides and aziridines, has become one of the most investigated strategies for the synthesis of cyclic carbonates and oxazolidin-2-ones. In this view, the following short account summarizes our recent results regarding the use of ruthenium porphyrin complexes and metal-free porphyrins, in combination with TBACl (tetrabutyl ammonium chloride), to promote the CO2 conversion into cyclic carbonates as well as N-alkyl and N-aryl oxazolidin-2-ones. Experimental data are described in combination with performed DFT studies that allowed proposing a reaction mechanism for the CO2 cycloaddition to aziridines promoted by metal-free porphyrins in which the adduct formed by TPPH2 and TBACl represents the real catalytic active species.
Carbon dioxide; Cyclic carbonates; Oxazolidin-2-ones; Porphyrins; Catalysis; DFT studies;
Settore CHIM/03 - Chimica Generale e Inorganica
24-set-2022
2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/969011
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