Photo-induced selective α/γ-functionalization of aliphatic amines via intramolecular hydrogen atom transfer

Abstract

A general method for site-selective α/γ-C(sp³)–H functionalization of amines has been developed. Regioselective activation of inert C–H bonds is achieved by 1,5/1,7-hydrogen atom abstraction by an oxidatively generated aryl radical. C-radicals thus formed at the α/γ-position of the amine functionality undergo radical conjugate addition to various Michael acceptors and provide the corresponding α/γ-functionalized amines. Good functional group tolerance, the success of gram-scale experiments and the late-stage modification of drug molecules greatly highlight the potential applicability of our method.