We have developed a mild photoinduced nickel-catalyzed arylation of remote C(sp3)–H bonds of aliphatic amines. This methodology proceeds via a hybrid aryl nickel-radical protocol, which concurrently merges the generation of a hybrid nickel-radical species, a hydrogen atom transfer (HAT) step, and nickel-catalyzed reductive C–C coupling to achieve a site-selective synthesis of remote arylated amines. The site-selectivity of HAT at the C(sp3)–H sites is controlled by the tethered auxiliary. This transformation is operationally simple, highly functional group tolerant, and has a broad scope that emphasizes the diverse applicability and the potential utilization of this methodology in the late-stage C(sp3)–H functionalization. The scope of this transformation will be presented, and a plausible mechanism discussed.

Photoinduced nickel-catalyzed arylation of remote C(sp3)–H bonds of amines

ACS Spring 2022

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