Chapter 3 Applied Suzuki cross-coupling reaction for syntheses of biologically active compounds

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. This reaction has been called the Suzuki coupling, Suzuki reaction, or Suzuki–Miyaura coupling. 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: (1) being largely unaffected by the presence of water, (2) tolerating a broad range of functional groups, (3) and proceeding generally regio- and stereoselectively. The inorganic by-product of the reaction is nontoxic and easily removed from the reaction mixture, thereby making the Suzuki coupling suitable for laboratories and also for industrial processes. A strategy to improve the efficiency of Suzuki coupling reactions is by combining fast microwave reaction with easy fluorous separation.. The Suzuki coupling reaction has been used to introduce a methyl group derived from commercially available methaneboronic acid into a vinyl triflate.