3-Trifluoromethyl Pyrrole Synthesis Based on ß-CF3-1,3-Enynamides.

A new metal-free method for the rapid, productive, and scalable preparation of 3-trifluoromethyl pyrroles has been developed. It is based on the electrophilic nature of the double bond of ß-CF3-1,3-enynamides due to the electron-withdrawing characteristics of the trifluoromethyl groups and the strong nucleophilic nature of alkyl primary amines. Evidence for the highly regioselective 1,4-hydroamination was observed after the isolation and characterization of the allenamide intermediate.