Chelation- assisted catalytic C- C, C- Si, and C- halogen bond formation by substitution via the cleavage of C(sp²)- H and C(sp³)- H bonds

Catalytic, regioselective C- H functionalizations have been extensively studied over the past two decades. In this account, we report our results on catalytic C- C, C- Si, and C- halogen bond formation reactions by substitution via the cleavage of C- H bonds. Catalytic arylation with arylboronates was developed and applied to the convenient synthesis of polycyclic aromatic hydrocarbons. Alkenylation reactions were also realized by the use of alkenylboronates and alkenyl esters. Various carbonyl- containing substituents were introduced using carbamoyl chlorides, alkyl chloroformates, acyl chlorides, and cyclic alkenyl carbonates. C- Si bonds were formed by reactions with hydrosilanes and vinylsilanes. C- H halogenation reactions were achieved by a combination of C- H bond cleavage and electrochemical oxidation and were applied to one- pot arylation reactions using the Suzuki- Miyaura coupling prodecure.