Formation of C–B, C–C, and C–X Bonds from Nonstabilized Aryl Radicals Generated from Diaryl Boryl Radicals

With the development of organoboron chemistry, boron-centered radicals have become increasingly attractive. However, their synthetic applications remain limited in that they have been used only as substrates for addition reactions or as initiators for catalytic reactions. We have achieved a new reaction pathway in which tetraarylborate salts are used as precursors for aryl radicals via boron radicals, by introducing a simple activation reagent. In addition, we carried out a diverse array of transformations involving these aryl radical precursors, which allowed the construction of new C–B, C–C, and C–X bonds in the presence of visible light.