Nickel-Catalyzed Cross-Coupling Reaction of Aryl Fluorides and Chlorides with Grignard Reagents under Nickel/Magnesium Bimetallic Cooperation

Naohiko Yoshikai, Hiroko Mashima, and Eiichi Nakamura*
Department of Chemistry, The University of Tokyo, and Nakamura Functional Carbon Cluster Project, ERATO, Japan Science and Technology Agency, Bunkyo-ku, Tokyo 113-0033, Japan
J. Am. Chem. Soc., 2005, 127 (51), pp 17978–17979
DOI: 10.1021/ja056327n
Publication Date (Web): December 1, 2005
Copyright © 2005 American Chemical Society
*

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

, nakamura@chem.s.u-tokyo.ac.jp

Abstract

Abstract Image

Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.

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History

  • Published In Issue December 28, 2005
  • Received September 14, 2005

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