Oxidative Homocoupling Reaction of Aryltrimethylsilanes by Pd/o-Chloranil Catalysis

A practical oxidative homocoupling reaction of aryltrimethylsilanes has been achieved by Pd/o-chloranil catalytic system. The reaction shows the good functional group tolerability toward bromo, fluoro, ester, and methoxy groups to give a series of biaryls bearing electron-withdrawing and -donating groups. The boronate group is also retained on biaryls without any Ar–B bond cleavage, which is highly advantageous for orthogonal coupling.