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Catalyst-Controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes via Aerobic Oxidative Heck Reactions

Changwu Zheng, Dian Wang and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

C. Zheng, D. Wang, S. S. Stahl, J. Am. Chem. Soc., 2012, 134, 16496-16499.

DOI: 10.1021/ja307371w (free Supporting Information)


Abstract

Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins in the presence of 2,9-dimethylphenanthroline as a ligand provides regioselective access to 1,3-disubstituted conjugated dienes in contrast to the observed regioselectivity from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene.

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Key Words

1,3-dienes


ID: J48-Y2012-3220