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Halogen Bond-Activated Visible-Light-Mediated Regioselective C-H Arylation of 2-Phenylimidazo-[1,2-a]pyridines.

An efficient method for transition metal-free halogen bond-assisted regioselective C-H arylation of 2-phenylimidazo-[1,2-a]pyridines under visible-light condition has been developed. The halogen bond between an aryl halide and base KOtBu initiates an electron transfer process and generates an aryl radical, which catalyzes its coupling with 2-phenylimidazo-[1,2-a]pyridines to give arylated products in good yield. Several control experiments, density functional theory calculations, and ultraviolet-visible analysis indicate the presence of a halogen bond between an aryl halide and KOtBu. This methodology has been successfully utilized to synthesize antileishmanial agents.