Cobalt(III)-Catalyzed Redox-Neutral Coupling of Acrylamides with Activated Alkenes via C–H Bond Activation

We would like to dedicate this work to Prof. Chien-Hong Cheng on the occasion of his 70^th birthday.

Abstract

A cobalt(III)-catalyzed coupling of substituted acrylamides with maleimides in the presence of 30 mol% pivalic acid providing olefin-migrated succinimide derivatives in a redox-neutral manner is described. The coupling reaction was examined with various substituted acrylamides and maleimides. The scope of the C–H alkylation reaction was also examined with substituted acrylates. A possible reaction mechanism involving a five-membered cobaltocycle as a key intermediate is proposed.

Key words

acrylamides - maleimides - C–H activation - alkylation - succinimides - acrylates - cobalt

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