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

Aryl azides have been used as atom-efficient nitrene transfer reagents in the (porphyrin) ruthenium-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 were achieved by using terminal olefins and aryl azides bearing electron-withdrawing groups on the aryl moiety. The reactions were influenced by steric factors. Internally disubstituted olefins exhibited a lower reactivity and tri- and tetra-substituted olefins did not react at all. A very high turnover number (TON) for the [Ru(TPP)CO] (TPP = tetraphenylporphyrin dianion) catalyzed animation of a-methylstyrene by p-nitrophenyl azide was obtained. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007.