Ligand-Controlled Regiodivergent Catalytic Amidation of Unactivated Secondary Alkyl Bromides

A regiodivergent Ni-catalyzed amidation of unactivated secondary alkyl bromides is described. The site-selectivity of the amidation event is dictated by subtle differences on the ligand backbone, allowing introduction of the amide function at either the original sp³ carbon–halide bond or at distal sp³ C–H sites within an alkyl side-chain via chain-walking scenarios.