Acylsilane represents a valuable synthon in synthetic chemistry. We report on ruthenium(II)-catalyzed ortho-C–H amination of aroylsilanes to provide facile access to synthetically useful imidobenzoylsilanes and tosyl-amidobenzoylsilanes. The protocols, with broad substrate scope and excellent functional group tolerance, are enabled with the weak chelation-assistance of acylsilane via C–H cyclometallation.