CROSS-COUPLING REACTIONS OF ORGANOTRIFLUOROBORATE SALTS

摘要

The Suzuki-Miyaura cross-coupling reaction is widely recognized as one of the most powerful and broadly utilized synthetic methods available for carbon-carbon bond formation. The importance of this coupling process has engendered a great deal of interest from practicing synthetic chemists both in academia and, because of the commercial importance of this reaction, in industry. Largely for historical reasons, boronic acids have become the standard reagents utilized for Suzuki-Miyaura cross-coupling reactions, and hundreds of these substances are now commercially available. Thousands of papers employing the reaction have been published, and many of these have been devoted to enhancements of the original procedure. Among the latter contributions, the vast majority of these important studies have dealt with improving the transformation by optimizing critical characteristics of the reaction such as the catalyst/ligand complex, the electrophile (aryl, heteroaryl, alkenyl, alkynyl, alkyl), the nucleofuge (chlorides, sulfonates, phosphates, esters), the solvent (e.g., water, ionic liquids), the bases required, and the conditions of the reaction (e.g., by using sonication or microwaves). Curiously, little effort was initially devoted to expand the scope of the reaction by altering the essential organoboron reagent. Organotrifmorobo-rates are one of several classes of organoboron reagents developed to provide a complementary suite of reagents for cross-coupling, affording alternatives to the classical boronic acid derivatives.