A Novel Uncatalyzed Insertion Reaction of In Situ Formed Trichlorosilyl Cyanide with Imines: A Facile Silicon Mediated Synthesis of α-Aminonitriles

Abstract

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 α-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 α, β-unsaturated aldimines 7a–e to give the corresponding 1,2-addition products 8a–e, in high yield, under exceedingly mild conditions.

Keywords:

• Tetrachlorosilane
• Aldimines
• Trichlorosilylcyanide
• Aminonitriles
• Synthesis