(Salen)Mn(III)-catalyzed chemoselective acylazidation of olefins

Abstract

We describe a (salen)Mn(iii)-catalyzed three-component reaction of aldehydes, olefins, and sodium azide for the installation of two useful groups (C═O and N3) into the double bond. Traditionally, (salen)Mn(iii) in conjunction with iodosobenzene is a classical catalysis system for epoxidation of olefins. Owing to the highly competitive oxygenation approaches, it is a true challenge to establish a distinct strategy for the exploration of new olefin transformations based on this (salen)Mn(iii) catalysis system. Herein, the key to this (salen)Mn(iii)-catalyzed acylazidation of olefins was the rational application of the distinct reactivity of oxomanganese(v) species which is capable of abstracting a hydrogen atom from a substrate C-H bond. This chemoselective reaction occurred in a precisely designed reaction sequence and tolerates complex molecular structures.