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Article
Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls
Journal of American Chemical Society
  • Marino A. Campo, Iowa State University
  • Haiming Zhang, Iowa State University
  • Tuanli Yao, Iowa State University
  • Abdellatif Ibdah, Iowa State University
  • Ryan D. McCulla, Iowa State University
  • Qinhua Huang, Iowa State University
  • Jian Zhao, Iowa State University
  • William S. Jenks, Iowa State University
  • Richard C. Larock, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
4-24-2007
DOI
10.1021/ja069238z
Abstract

A novel 1,4-palladium migration between the o- and o‘-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C−H acidity of the available arene positions.

Comments

Reprinted (adapted) with permission from Journal of American Chemical Society, 129(19); 6298-6307. Doi: 10.1021/ja069238z. Copyright 2007 American Chemical Society.

Rights
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Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Marino A. Campo, Haiming Zhang, Tuanli Yao, Abdellatif Ibdah, et al.. "Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls" Journal of American Chemical Society Vol. 129 Iss. 19 (2007) p. 6298 - 6307
Available at: http://works.bepress.com/william_jenks/16/