Cobalt-catalyzed regioselective diazidation of 1-aryl-1,3-dienes enabled by a single electron transfer/radical addition/group transfer relay process†

Abstract

A novel cobalt-catalyzed 1,2-diazidation of 1-aryl-1,3-dienes by using TMSN₃ as an azide source has been reported. A series of vicinal diazides containing unsaturated bonds that are amenable to further functionalization were synthesised with excellent regioselectivity and stereoselectivity under mild conditions. Preliminary mechanistic studies suggest that the reaction proceeds via a single electron transfer/radical addition/group transfer relay process.