Copper-Catalyzed Direct sp2 C-H Silylation of Arylamides Using Disilanes.

Abstract

A copper-catalyzed method for direct intermolecular ortho-silylation of benzamides has been developed that affords organosilane products in moderate to high yields. The key features include: (i) use of commercially available disilanes as a silicon source with 8-aminoquinoline as a bidentate directing group, (ii) use of earth-abundant first-row transition metal, (iii) operationally simple conditions without the need of an inert atmosphere, and (iv) tolerance of a wide range of functional groups. The practicality and effectiveness of this method have been demonstrated by a gram-scale experiment. This strategy, therefore, constitutes a convenient way of constructing C-Si bonds useful for synthetic organic chemistry.