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.