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

Shifang Liu,† Neil Berry,† Nick Thomson,‡ Alan Pettman,‡ Zeynab Hyder,† Jun Mo,† and Jianliang Xiao*†
Department of Chemistry, Liverpool Centre for Materials and Catalysis, University of Liverpool, Liverpool L69 7ZD, U.K., and Chemical Research and Development Department, Pfizer Global Research and Development, Ramsgate Road, Sandwich, Kent CT13 9NJ, U.K. j.xiao@liv.ac.uk
J. Org. Chem., 2006, 71 (19), pp 7467–7470
DOI: 10.1021/jo0609632
Publication Date (Web): August 18, 2006
Copyright © 2006 American Chemical Society
†

 University of Liverpool.

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‡

 Pfizer Global Research and Development.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

meso-2,4-Bis(diphenylphosphino)pentane (mBDPP) has proved to be an effective regiocontrolling ligand for palladium-catalyzed internal arylation by aryl bromides of electron-rich olefins in a common solvent DMSO with no need for any halide scavengers. The arylation of the benchmark electron-rich olefin butyl vinyl ether took place smoothly to afford exclusively α-arylated product with high isolated yields. The better performance of mBDPP, compared with that of the commonly used DPPP [1,3-bis(diphenylphosphino)propane], highlights the important but subtle effect of ligand on the regioselectivity of the Heck arylation reactions.

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History

  • Published In Issue September 15, 2006
  • Received May 9, 2006

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