4.8 Article

Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 13, 页码 5248-5253

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000224

关键词

amides; cross-coupling; nickel catalysis; photoredox catalysis; radical chemistry

资金

  1. MICIU [CTQ2016-75520-P]
  2. AGAUR [2017 SGR 981]
  3. European Research Council [ERC-2015-CoG 681840 - CATA-LUX]
  4. H2020-MSCA-ITN-2016 [722591 -PHOTO-TRAIN]
  5. MINECO [CTQ2013-45938-P]

向作者/读者索取更多资源

Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.

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