A Study On The Radical Chain Addition Reaction Of N-aryl-trifluoroacetimidoyl Chlorides And Related Derivazation

Owing to the inherent structure of the molecule,the N-aryl-trifluoroacetimidoyl chloride tends to undergo a nucleophilic substitution reaction to afford the targeting molecule by building the corresponding intermediate.Many heterocycles such as indoles,quinolines and imidazoles could be synthesized from this method.The construction of indole derivatives has become an attractive field due to their wide occurrence in natural products and pharmaceutical molecules.Meanwhile,more and more thorough researches based on radical reaction were reported when it comes to the radical addition to multiple bonds.Our lab has recently discovered an azobisisobutyronitrile(AIBN)and tert-dodecyl mercaptan(TDM)as co-catalyst to initiate radical chain addition of 1,3-dioxolane to imines,the yield is up to 96%.Based on these theories and studies,we report an AIBN/NHS catalyzed radical addition of 1,3-dioxolane to different types of N-Aryl-trifluoroacetimidoyl chlorides with distinguishing products.According to the mechanistic studies,this reaction is controlled by the radical polar effect.We get an convenient method to synthesis the indole in the derivatizations,which has the potential application in many natural products and pharmaceutical compounds.