An iron-catalyzed, N-H imine-directed arene C-H silylation reaction with hydrosilane has been achieved. Pivalophenone N-H imine undergoes ortho C-H silylation with triethylsilane in the presence of [Fe3(CO)12] as a catalyst and norbornene as a hydrogen acceptor. The product can be readily transformed into ortho-silylated benzonitrile via conversion of the imine functionality to a cyano group under peroxide photolysis.