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Regioselective Heck Vinylation of Electron-Rich Olefins with Vinyl Halides: Is the Neutral Pathway in Operation?

Matthew McConville, Ourida Saidi, John Blacker and Jianliang Xiao*

*Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K., Email: j.xiaoliv.ac.uk

M. McConville, O. Saidi, J. Blacker, J. Xiao, J. Org. Chem., 2009, 74, 2692-2698.

DOI: 10.1021/jo802781m (free Supporting Information)


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Abstract

Highly regioselective vinylation of electron-rich olefins by halostyrenes is effected by palladium catalysis with either mono- or bidentate phosphines in DMSO as solvent. The use of hemilabile 1,3-bis(diphenylphosphino)propane monoxide as a ligand led to faster reactions of more challenging 2-substituted vinyl ethers and reduced Pd loadings.

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Pd-mBDPP-Catalyzed Regioselective Internal Arylation of Electron-Rich Olefins by Aryl Halides

S. Liu, N. Berry, N. Thomson, A. Pettman, Z. Hyder, J. Mo, J. Xiao, J. Org. Chem., 2006, 71, 7467-7470.


Key Words

Enones, Heck Reaction


ID: J42-Y2009-0980