ZnI2-Catalyzed Aminotrifluoromethylation Cyclization of Alkenes Using PhICF3Cl

We report here an alternatively catalytic aminotrifluoromethylation of alkenes using PhICF3Cl as a bifunctional reagent along with ZnI2 as a dual catalyst. A combined catalytic strategy was established for the intramolecular aminotrifluoromethylation of 4-pentenamines. As a result, a set of 2-trifluoroethyl-pyrrolidines was obtained in a high selectivity. Mechanism studies revealed that the reaction included an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a sequential Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.

Automated summary

An effective method for the aminotrifluoromethylation of alkenes was developed by using PhICF3Cl and ZnI2 as catalysts. The mechanism studies showed that the reaction involves an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.