Trichlorosilane-imine complexes. A new method for the reduction of imines to amines

It has been found that trichlorosilane adds regio-specifically to the carbon-nitrogen double bond of imines under mild conditions to yield hydrolytically unstable N-trichlorosilyl intermediates. The latter can be hydrolyzed in situ by alcoholic base to give the corresponding amines in moderate to good yields. Variously substituted aldo and keto imines, both alkyl and aryl, were tested to demonstrate the scope of the reaction. The facility of trichlorosilane addition appears to depend on the nature of the groups directly attached to the carbon-nitrogen double bond. Hydride trapping experiments suggest an intramolecular rather than intermolecular hydride transfer during the course of the reaction.