C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

We describe the functionalization of α-amino C–H bonds with aryl halides using a combination of nickel and photoredox catalysis. This direct C–H, C–X coupling uses inexpensive and readily available starting materials to generate benzylic amines, an important class of bioactive molecules. Mechanistically, this method features the direct arylation of α-amino radicals mediated by a nickel catalyst. This reactivity is demonstrated for a range of aryl halides and N-aryl amines, with orthogonal scope to existing C–H activation and photoredox methodologies. We also report reactions with several complex aryl halides, demonstrating the potential utility of this approach in late-stage functionalization.