Catalytic metal-free Si-N cross-dehydrocoupling

The metal-free B(C6F5)(3) catalyzed dehydrocoupling of hydrosilanes with anilines, carbazoles and indoles is reported. For anilines and carbazoles the reaction proceeds by the liberation of H-2 as the sole Si-N coupling byproduct. Indoles react with diphenyl(methyl) hydrosilane to give N-silyl indolines with high diastereoselectivity (d.r. 10 : 1) in excellent yields. A mechanism for this Si-N coupling/hydrogenation sequence is proposed.