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Rhodium(III)‐Catalyzed ortho Alkenylation of N ‐Phenoxyacetamides with N ‐Tosylhydrazones or Diazoesters through CH Activation
Author(s) -
Hu Fangdong,
Xia Ying,
Ye Fei,
Liu Zhenxing,
Ma Chen,
Zhang Yan,
Wang Jianbo
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309650
Subject(s) - chemistry , carbene , rhodium , catalysis , stereoselectivity , medicinal chemistry , migratory insertion , organic chemistry
A coupling reaction of N ‐phenoxyacetamides with N ‐tosylhydrazones or diazoesters through Rh III ‐catalyzed CH 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.