Organotrifluoroborates have been utilized as an alternative to other organoboron species for a variety of cross-coupling reactions. The tetracoordinated nature of these compounds makes them resistant to a variety of common employed reagents such as acids, bases and oxidants. Moreover, organotrifluoroborates are moisture and air stable. In contrast to their boronic acid counterparts, heteroaryltrifluoroborates can be stored on the bench top for years without appreciable decomposition. Therefore, organotrifluoroborates can be utilized to build molecular complexity in a molecule, with subsequent transformation of the carbon-boron bond into a variety of functional groups.The terminal hydrolysis, oxidation, chlorination and nitrosation of organotrifluoroborates have been studied in our laboratory. The methods developed proved to be mild, fast, and efficient for a variety of aryl and heteroaryl systems, and in some cases for alkenyl and alkyltrifluoroborates. These metal-free transformations were conducted in an open atmosphere, and the products were obtained in high purity, thereby avoiding the extensive purification steps often required for other boron species.

Metal-free hydrolysis, oxidation, chlorination, and nitrosation of potassium organotrifluoroborates

244th National Meeting (2012)

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