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Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

Jared H. Delcamp, Paul E. Gormisky and M. Christina White*

*University of Illinois Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States, Email: whitescs.uiuc.edu

J.-J. Dai, C. Fang, B. Xiao, J. Yi, J. Xu, Z.-J. Liu, X. Lu, L. Liu, Y. Fu, J. Am. Chem. Soc., 2013, 135, 8436-8439.

DOI: 10.1021/ja402891m (free Supporting Information)


Abstract

An oxidative Heck reaction enables a selective formation of complex dienes and polyenes from nonactivated terminal olefins and slight excesses of vinyl boronic esters that feature diverse functionality. 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.

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Key Words

Dienes, Benzoquinone


ID: J48-Y2013