Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998

Abstract

The palladium-catalyzed cross-coupling reaction between organoboron compounds and organic halides or triflates provides a powerful and general methodology for the formation of carbon–carbon bonds. Recently, this reaction has been called the Suzuki coupling, Suzuki reaction, or Suzuki–Miyaura coupling, although we never referred to it as such previously. In this review, this name will be used with hesitation, simply in order to express the coupling reaction. The availability of the reagents and the mild reaction conditions all contribute to the versatility of this reaction. The coupling reaction offers several additional advantages, such as being largely unaffected by the presence of water, tolerating a broad range of functional groups, and proceeding generally regio- and stereoselectively. Moreover, the inorganic by-product of the reaction is non-toxic and easily removed from the reaction mixture thereby making the Suzuki coupling suitable not only for laboratories but also for industrial processes. We published previously a comprehensive review of the reaction (see N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457 and A. Suzuki, in: F. Diederich, P.J. Stang, (Eds.), Metal-Catalyzed Cross-coupling Reactions, VCH, Weinheim, 1998, pp. 49–97), which covered mainly the references until the end of 1994. Thereafter, a large number of papers related to the coupling reaction have been reported. Consequently, such new results presented from 1995 to May 1998 are summarized in this review.