Chelation-Assisted Regioselective Catalytic Functionalization of C-H, C-O, C-N and C-F Bonds

Transition-metal-catalyzed functionalization of unreactive carbon bonds such as C-H, C-O, C-N, and C-F bonds has been extensively studied over the last two decades. In this account we describe our studies on chelation-assisted catalytic transformations of unreactive carbon bonds in aromatic and olefinic compounds. Various C-C bond forming reactions are achieved by catalytic addition of C-H bonds to alkenes and alkynes, and via coupling reactions such as those of C-H, C-O, C-N, and C-F bonds with boronic esters. Methods for the conversion of C-H bonds into C-Si and C-X (X = halogen) bonds are also developed. The C-C bond forming reactions are applied to short syntheses of polycyclic aromatic hydrocarbons.