Orthogonal Selectivity in C–H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution

Oxidative
coupling is a useful tool to synthesize vinylarenes.
Despite remarkable successes in linear vinylarene, branched vinylarene
synthesis has remained underdeveloped. Overcoming this limitation,
herein, we report a chelation-assisted oxidative coupling to generate
branched olefinated product in high yield. Exclusive branched selectivity
was obtained using alkenyl carboxylic acid. Detailed experimental
studies combined with computational investigations suggest that β-migratory
insertion, followed by a decarboxylation pathway is operative for
the overall transformation.