Copper(II)-Photocatalyzed N–H Alkylation with Alkanes

Abstract

We report a practical method for the alkylation of N–H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)–H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N–H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.