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

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posted on 2019-09-25, 17:34 authored by Soumitra Agasti, Bhaskar Mondal, Tapas Kumar Achar, Soumya Kumar Sinha, Anjana Sarala Suseelan, Kalman J. Szabo, Franziska Schoenebeck, Debabrata Maiti
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.