4.8 Article

Carboxy Group as a Remote and Selective Chelating Group for C-H Activation of Arenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 51, Pages 18502-18507

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910691

Keywords

arylation; C-H activation; coordination modes; palladium; synthetic methods

Funding

  1. NSFC [21871257, 21702206]
  2. Natural Science Foundation of Fujian Province [2017J06007, 2017J05038]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. 100 Talents Program of Fujian Province

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The first example of carboxy group assisted, remote-selective C(sp(2))-H activation with a Pd-II catalyst has been developed and proceeds through a possible kappa(2) coordination of the carboxy group, thus suppressing the ortho-C-H activation through kappa(1) coordination. Besides meta-C-H olefination, direct meta-arylation of hydrocinnamic acid derivatives with low-cost aryl iodides has been achieved for the first time. These findings may motivate the exploration of novel reactivities of the carboxy assisted C-H activation reactions with intriguing selectivities.

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