4.8 Article

Rhodium-Catalyzed Transarylation of Benzamides: C-C Bond vs C-N Bond Activation

Journal

ACS CATALYSIS
Volume 10, Issue 5, Pages 3398-3403

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b05214

Keywords

amide; C-C activation; C-H activation; arylation; rhodium catalysis; DFT

Funding

  1. National Natural Science Foundation of China [21472128]
  2. Sichuan Science and Technology Program [2018JY560]

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A rhodium-catalyzed transarylation of benzamides via selective C-C bond activation with arylboronic acids was described, which was distinct from the conventional metal-catalyzed C-N bond activation. This transformation exhibited good functional group compatibility with yields up to 88%, offering a practical approach for the construction and functionalization of benzamides. Preliminary experimental and computational studies revealed the selectivity of metal insertion into the C-C bond or the C-N bond was greatly affected by substituents on the amide's N atom.

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