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J Am Chem Soc. 2007 May 16;129(19):6298-307. Epub 2007 Apr 24.

Aryl to aryl palladium migration in the Heck and Suzuki coupling of o-halobiaryls.

Author information

  • 1Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.

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.

PMID:
17451243
[PubMed]
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