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Palladium-Catalyzed Hydroarylation of 1,3-Dienes with Boronic Esters via Reductive Formation of π-Allyl Palladium Intermediates under Oxidative Conditions

Longyan Liao and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, Email: sigmanchem.utah.edu

L. Liao, M. S. Sigman, J. Am. Chem. Soc., 2010, 132, 10209-10211.

DOI: 10.1021/ja105010t


Abstract

Generation of a π-allyl Pd species directly from a 1,3-diene via a Pd-catalyzed aerobic alcohol oxidation enables a palladium-catalyzed reductive cross-coupling of 1,3-dienes with boronic esters. Both the scope of the process and the origin of a highly selective 1,2-addition are discussed.

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Key Words

substituted arenes


ID: J48-Y2010-2010