Journal
ACS CATALYSIS
Volume 11, Issue 16, Pages 10223-10227Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02913
Keywords
nickel; regiodivergent; amide bond; alkyl bromide; chain walking
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Funding
- ICIQ
- FEDER/MICIU [AEI/PGC2018-096839-B100]
- MCI/AIE [CEX2019-000925-S]
- FPU
- FPI
- European Union's Horizon 2020 under the Marie Curie PREBIST grant [754558]
- 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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