1. Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls
- Author
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Abdellatif Ibdah, Haiming Zhang, Marino A. Campo, Jian Zhao, Tuanli Yao, Qinhua Huang, William S. Jenks, Ryan D. McCulla, and Richard C. Larock
- Subjects
Reaction conditions ,Chemistry ,Aryl ,chemistry.chemical_element ,General Medicine ,General Chemistry ,Biochemistry ,Catalysis ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Suzuki reaction ,Heck reaction ,Organopalladium ,Polymer chemistry ,Organic chemistry ,Ethyl acrylate ,Palladium - 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.
- Published
- 2007
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