Rhodium-catalyzed intermolecular dehydrogenative C-H silylation of unactivated arenes affords silylarenes in good yields with high steric regiocontrol. The advantages of this method over previous methods for silylation of aromatic C-H bonds include low reaction temperature (45 �C), excellent regioselectivity derived from the steric effects of substituents on the substrates and of the ligands, high yields with arene as the limiting reagent, and the synthetic versatility of the silylarene products. Mechanistic studies reveal an unusual Rh(III) complex as the catalyst resting state. The proposed reaction mechanism and its implications on designing C-H activation catalysts will be discussed.

Transition metal-catalyzed C-H silylation of arenes: Regioselectivity and mechanisms

248th National Meeting (2014)

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