4.8 Article

Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 5, Pages 1364-1367

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309650

Keywords

C-H activation; diazo compounds; homogeneous catalysis; metal-carbene complexes; migratory insertion

Funding

  1. National Basic Research Program of China (973 Program) [2012CB821600]
  2. National Natural Science Foundation of China [21272010, 21332002]

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A coupling reaction of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through Rh-III-catalyzed C-H activation is reported. In this reaction, ortho-alkenyl phenols were obtained in good yields and with excellent regio- and stereoselectivity. Rh-carbene migratory insertion is proposed as the key step in the reaction mechanism.

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