This work describes the aziridination process of a-methylstyrene by using electron poor aromatic azides in the presence of metal-based porphyrins as catalysts. Different ruthenium and cobalt-based porphyrins were successfully employed for the synthesis of N-aryl aziridines performed under a traditional batch methodology and under continuous flow conditions. In general, yields obtained using ruthenium-based catalysts in a traditional batch process were higher than those observed when the reaction was performed under flow conditions. However, cobalt-based porphyrins showed better activities and short reaction times when employed in a flow system process. DFT calculations were also performed in order to understand the influence of substituents on the porphyrin ring in the aziridination process.

Metal-porphyrin catalyzed aziridination of alpha-methylstyrene: Batch vs. flow process / D. Intrieri, S. Rossi, A. Puglisi, E. Gallo. - In: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES. - ISSN 1088-4246. - 21:4-6(2017), pp. 381-390. [10.1142/S1088424617500365]

Metal-porphyrin catalyzed aziridination of alpha-methylstyrene: Batch vs. flow process

D. Intrieri;S. Rossi;A. Puglisi;E. Gallo
2017

Abstract

This work describes the aziridination process of a-methylstyrene by using electron poor aromatic azides in the presence of metal-based porphyrins as catalysts. Different ruthenium and cobalt-based porphyrins were successfully employed for the synthesis of N-aryl aziridines performed under a traditional batch methodology and under continuous flow conditions. In general, yields obtained using ruthenium-based catalysts in a traditional batch process were higher than those observed when the reaction was performed under flow conditions. However, cobalt-based porphyrins showed better activities and short reaction times when employed in a flow system process. DFT calculations were also performed in order to understand the influence of substituents on the porphyrin ring in the aziridination process.
homogeneous catalysis; ruthenium; cobalt; aziridination; azide; flow chemistry
Settore CHIM/03 - Chimica Generale e Inorganica
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/512877
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