Hydroazidation of trifluoromethyl alkenes with trimethylsilyl azide enabled by organic photoredox catalysis

Abstract

Herein, we report an organic photoredox-catalyzed hydroazidation of trifluoromethyl alkenes with user-friendly trimethylsilyl azide (TMSN₃), enabling a direct access to a broad range of valuable β-CF₃-azides with exclusive selectivity under mild reaction conditions. The synthetic utility of this reaction was demonstrated by the late-stage modification of complex drug derivatives, scale-up of the reaction and diverse further derivatizations of the β-CF₃-azide product.