Stereoselective Direct N-Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent, János T. Csenki, Ádám Mészáros, Zsombor Gonda, Zoltán Novák, Chem. Eur. J. 2021, 27, 15638-15643. DOI: 10.1002/chem.202102840 | [Full Text Link] [Supp. Info. Link]

The availability and synthesis of fluorinated enamine derivatives such as N-(3,3,3-trifluoropropenyl)heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, we describe a stereoselective N-trifluoropropenylation method based on the use of a bench-stable trifluoropropenyl iodonium salt. This reagent enables the straightforward trifluoropropenylation of various N-heterocycles under mild reaction conditions, providing trifluoromethyl enamine type moieties with high stereoselectivity and efficiency.