Regioselective N–F and α C(sp3)–H Arylation of Aliphatic N-Fluorosulfonamides with Imidazopyridines

A regioselective arylation of aliphatic N-fluorosulfonamides with imidazopyridines enabled by breaking of N–F and α C­(sp3)–H bond to form C–N and C–C bonds was described. With CuCl as the catalyst, a radical mechanism was proposed to produce N-arylated aliphatic sulfonamides via a N radical intermediate. Importantly, under acidic conditions, an in situ generated imine was the possible intermediate, which was trapped by imidazopyridines to form α C­(sp3)–H arylated aliphatic sulfonamides. The current protocol featured a broad substrate scope, tunable reaction conditions, operational convenience, and good regioselectivity.