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 sp(3) carbon-halide bond or at distal sp(3) C-H sites within an alkyl side-chain via chain-walking scenarios.

Automated summary

A region-divergent Ni-catalyzed amidation of unactivated secondary alkyl bromides is described in this study, with site-selectivity of the amidation event dictated by subtle differences on the ligand backbone, enabling introduction of the amide function at either the original sp(3) carbon-halide bond or at distal sp(3) C-H sites within an alkyl side-chain via chain-walking scenarios.