The protonation of commercially available porphyrin ligands yields a class of bifunctional catalysts able to promote the synthesis of N-alkyl oxazolidinones by the CO2 cycloaddition to corresponding aziridines. The catalytic system does not require the presence of any Lewis base or additive and shows interesting features both in terms of cost-effectiveness and eco-compatibility. The metal-free methodology is active by using the low catalytic loading of 1% mol and the chemical stability of the protonated porphyrin allowed its recycle for three consecutive times without any decrease of performances. In addition, a DFT study was performed in order to suggest how a simple protonated porphyrin can mediate the CO2 cycloaddition to aziridines yielding oxazolidinones.

Protonated Porphyrins: Bifunctional Catalysts for the Metal-Free Synthesis of N-Alkyl-Oxazolidinones / M. Cavalleri, C. Damiano, G. Manca, E. Gallo. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 29:1(2023 Jan 02), pp. e2022027.1-e2022027.7. [10.1002/chem.202202729]

Protonated Porphyrins: Bifunctional Catalysts for the Metal-Free Synthesis of N-Alkyl-Oxazolidinones

M. Cavalleri
Primo
;
C. Damiano
Secondo
;
E. Gallo
2023

Abstract

The protonation of commercially available porphyrin ligands yields a class of bifunctional catalysts able to promote the synthesis of N-alkyl oxazolidinones by the CO2 cycloaddition to corresponding aziridines. The catalytic system does not require the presence of any Lewis base or additive and shows interesting features both in terms of cost-effectiveness and eco-compatibility. The metal-free methodology is active by using the low catalytic loading of 1% mol and the chemical stability of the protonated porphyrin allowed its recycle for three consecutive times without any decrease of performances. In addition, a DFT study was performed in order to suggest how a simple protonated porphyrin can mediate the CO2 cycloaddition to aziridines yielding oxazolidinones.
porphyrin* carbon dioxide * aziridine * oxazolidinone * DFT study
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
PSRL220LPRAT_01 - Piano di Sostegno alla Ricerca 2015-2017 - Linea 2 "Dotazione annuale per attività istituzionali" (anno 2020) - PRATI, LAURA - PSR_LINEA2_ / Piano di sviluppo di ricerca - Dotazioni dipartimentali - Linea 2 - 2020
4-ott-2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/944473
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