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Updated: Jan 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Aerobic Oxidative Cross-Coupling of Substituted Acrylamides with Alkenes Catalyzed by an Electron-Deficient CpRhIII
Ryo Yoshimura1, Yu Shibata1, Ken Tanaka1
1Department of Chemical Science and Engineering , Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8550 , Japan.
Abstract:
It has been established that an electron-deficient CpRhIII complex, bearing two ester moieties on the Cp ring, [CpERhIII], catalyzes the aerobic oxidative cross coupling of substituted acrylamides with both activated and unactivated alkenes, leading to (2Z,4E)-dienamides, at relatively low temperature (80 °C). Importantly, tertiary, secondary, and primary amide directing groups could equally be used in this catalysis. The mechanistic studies revealed that the electron-deficient nature of the CpERhIII complex facilitates the turnover-limiting vinylic C-H bond cleavage of the acrylamides.
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