Aerobic Oxidative Cross-Coupling of Substituted Acrylamides with Alkenes Catalyzed by an Electron-Deficient CpRhIII Complex.

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.