Aryl azides are atom-efficient nitrene transfer reagents in the ruthenium porphyrin catalyzed amination of olefins. Several azides, olefins and Ru(porphyrin)CO complexes were tested to investigate the scope and limits of the reaction. Quantitative yields and short reaction times have been achieved using terminal olefins and aryl azides bearing electron withdrawing groups on the aryl moiety. The reaction is influenced by steric factors. Internal di-substituted olefins showed a lower reactivity and tri- and tetra-substituted ones did not react at all. A very high TON for the Ru(TPP)CO (TPP = dianion of tetraphenylporphyrin) catalyzed amination of  methylstyrene by 4 nitrophenyl azide was obtained.

The (porphyrin)ruthenium-catalyzed aziridination of olefins using aryl azides as nitrogen sources / S. Fantauzzi, E. Gallo, A. Caselli, C. Piangiolino, F. Ragaini, S. Cenini. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :36(2007), pp. 6053-6059. [10.1002/ejoc.200700678]

The (porphyrin)ruthenium-catalyzed aziridination of olefins using aryl azides as nitrogen sources

S. Fantauzzi;E. Gallo;A. Caselli;C. Piangiolino;F. Ragaini;S. Cenini
2007

Abstract

Aryl azides are atom-efficient nitrene transfer reagents in the ruthenium porphyrin catalyzed amination of olefins. Several azides, olefins and Ru(porphyrin)CO complexes were tested to investigate the scope and limits of the reaction. Quantitative yields and short reaction times have been achieved using terminal olefins and aryl azides bearing electron withdrawing groups on the aryl moiety. The reaction is influenced by steric factors. Internal di-substituted olefins showed a lower reactivity and tri- and tetra-substituted ones did not react at all. A very high TON for the Ru(TPP)CO (TPP = dianion of tetraphenylporphyrin) catalyzed amination of  methylstyrene by 4 nitrophenyl azide was obtained.
azides; aziridines; ruthenium; porphyrins; catalysis
Settore CHIM/03 - Chimica Generale e Inorganica
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/40689
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