Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

JH Delcamp, PE Gormisky…

Index: Delcamp, Jared H.; Gormisky, Paul E.; White, M. Christina Journal of the American Chemical Society, 2013 , vol. 135, # 23 p. 8460 - 8463

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Citation Number: 33

Abstract

We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd (II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse ...