Photoredox cross-dehydrogenative C(sp2)–C(sp3) coupling of heteroarenes with secondary amines through 1,5-HAT

Abstract

The functionalization of α-C(sp³)–H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis α-C(sp³)–H bond functionalization in alicyclic and aliphatic secondary amines facilitated by intramolecular 1,5-hydrogen atom transfer (HAT). This finding unlocks a sustainable method for rapidly constructing complex heterocyclics via cross-dehydrogenative C–C coupling of protected amines and nitrogen-containing heterocycles. This protocol boasts broad applicability to various substrates, exhibits tolerance to numerous functional groups, and supports the late-stage modification of drug molecules.