A novel uncatalyzed insertion reaction of in situ formed trichlorosilyl cyanide with imines: A facile silicon mediated synthesis of alpha-aminonitriles

The tetrachlorosilane-potassium cyanide reagent combination, trichloro-silyl cyanide-in situ) is a new, safe and versatile hydrogen cyanide substitute. The reaction of this reagent with saturated aldimines 1a-j and benzophenone oxime 3, in absences of any catalyst, affords the corresponding alpha-aminonitriles 2a-j and 4, respectively, in excellent, yield. Under the same condition the bis-imine 5 yields the imidazo[1,2-a]quinoxaline derivative 6. Moreover, trichlorosilyl cyanide-in situ undergoes regiospecific addition onto alpha, beta-unsaturated aldimines 7a-e to give the corresponding 1,2-addition products 8a-e, in high yield, under exceedingly mild conditions.