Pd-catalyzed homologation of arylboronic acids as a platform for the diversity-orientated synthesis of benzylic C–X bonds

We report a synthetic platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful intermediates but commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation arylboronic acids provides access these compounds that, in turn, allow C–C, C–O, and C–N bonds from Pd- Cu-mediated cross-coupling or oxidative processes. This affords wide variety alcohols, diarylmethanes, benzyl amines, ethers. Limitations disclosed utility is further demonstrated by generation analogues meclizine.