Visible-Light-Irradiated Multicomponent Reactions of Aliphatic Amines, Propiolate Acid Esters, and CF3 SO2 Na for Accessing β-CF3 Enamines.

Abstract

A novel one-pot two-step multicomponent reaction has been achieved for the preparation of β-CF3 enamines by using different aliphatic amines, propiolates, and CF3 SO2 Na as starting material. In this protocol, various aliphatic amines including primary amines, cyclic or acyclic secondary amines were demonstrated to be good coupling partners, and different β-CF3 enamines were obtained in moderate to good yields. Among them, the primary aliphatic amines only gave pure (E)-β-CF3 enamines as products. The synthetic utility of the MCRs strategy was further demonstrated by mild conditions, gram-scale synthesis and natural sunlight-induced protocol. Preliminary mechanistic studies suggest that this trifluoromethylation of C(sp2 )-H involves radical process.