The covalently heterogenisation of a free-base porphyrin on SBA-15 silica yielded TPPH2@SBA-15 (TPPH2 = tetraphenyl porphyrin), which was very efficient to promote the CO2 cycloaddition to three-membered rings. The TPPH2@SBA-15/TBAX-based catalytic procedure was very general, as revealed by excellent activities registered in the reaction of CO2 with epoxides, N-alkyl and N-aryl aziridines, forming cyclic carbonates, N-alkyl and N-aryl oxazolidinones, respectively. It is worth noting that this is the first example of the heterogeneously catalysed synthesis of N-aryl oxazolidinones from corresponding N-aryl aziridines. The scale-up of the methodology highlighted that catalytic performances of all the three investigated reactions were maintained also working at a gram-scale to pave the way for future developments of the procedure. In addition, the recycle of TPPH2@SBA–15 for several consecutive reactions was efficient and observed catalytic activities were very similar to those registered in the presence of a fresh material. All the acquired data indicated an excellent sustainability of the catalytic protocol to envisage upcoming practical applications.

A metal-free porphyrin heterogenised onto SBA-15 silica: A performant material for the CO2 cycloaddition to epoxides and aziridines / P. Sonzini, N. Berthet, C. Damiano, V. Dufaud, E. Gallo. - In: JOURNAL OF CATALYSIS. - ISSN 0021-9517. - 414:(2022), pp. 143-154. [10.1016/j.jcat.2022.08.036]

A metal-free porphyrin heterogenised onto SBA-15 silica: A performant material for the CO2 cycloaddition to epoxides and aziridines

P. Sonzini
Primo
;
C. Damiano;E. Gallo
Ultimo
2022

Abstract

The covalently heterogenisation of a free-base porphyrin on SBA-15 silica yielded TPPH2@SBA-15 (TPPH2 = tetraphenyl porphyrin), which was very efficient to promote the CO2 cycloaddition to three-membered rings. The TPPH2@SBA-15/TBAX-based catalytic procedure was very general, as revealed by excellent activities registered in the reaction of CO2 with epoxides, N-alkyl and N-aryl aziridines, forming cyclic carbonates, N-alkyl and N-aryl oxazolidinones, respectively. It is worth noting that this is the first example of the heterogeneously catalysed synthesis of N-aryl oxazolidinones from corresponding N-aryl aziridines. The scale-up of the methodology highlighted that catalytic performances of all the three investigated reactions were maintained also working at a gram-scale to pave the way for future developments of the procedure. In addition, the recycle of TPPH2@SBA–15 for several consecutive reactions was efficient and observed catalytic activities were very similar to those registered in the presence of a fresh material. All the acquired data indicated an excellent sustainability of the catalytic protocol to envisage upcoming practical applications.
Aziridine; Carbon Dioxide; Cycloaddition; Epoxide; Heterogenised porphyrin
Settore CHIM/03 - Chimica Generale e Inorganica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/944477
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