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A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction

Jared H. Delcamp, Alexandria P. Brucks and M. Christina White*

*University of Illinois Urbana−Champaign, 600 S. Mathews, Urbana, Illinois 61801, Email: whitescs.uiuc.edu

J. H. Delcamp, A. P. Brucks, M. C. White, J. Am. Chem. Soc., 2008, 130, 11270-11271.

DOI: 10.1021/ja804120r (free Supporting Information)



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Abstract

A chelate-controlled intermolecular oxidative Heck reaction proceeds with a wide range of nonresonance stabilized α-olefin substrates and organoboron reagents to afford internal olefin products in good yields and outstanding regio- and E:Z stereoselectivities. Pd-H isomerization, common in many Heck reactions, is not observed under these mild, oxidative conditions.

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Key Words

Oxidative Heck Reaction, Olefination, Benzoquinone


ID: J48-Y2008-2260