4.8 Article

Ligand-Controlled Regiodivergent Catalytic Amidation of Unactivated Secondary Alkyl Bromides

Journal

ACS CATALYSIS
Volume 11, Issue 16, Pages 10223-10227

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02913

Keywords

nickel; regiodivergent; amide bond; alkyl bromide; chain walking

Funding

  1. ICIQ
  2. FEDER/MICIU [AEI/PGC2018-096839-B100]
  3. MCI/AIE [CEX2019-000925-S]
  4. FPU
  5. FPI
  6. European Union's Horizon 2020 under the Marie Curie PREBIST grant [754558]
  7. Sao Paulo Research Fundation [FAPESP 2019/015606]

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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.
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.

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