N-CF₃ Imidoyl Chlorides: Scalable N-CF₃ Nitrilium Precursors for the Construction of N-CF₃ Compounds

Abstract

A wide range of N-CF 3 imidoyl chlorides were synthesized for the first time via the N-trifluoromethylation of nitriles in DCM by using AlCl 3 -activated PhICF 3 Cl as the CF 3 source. The reactions of them with N-/O-/S-nucleophiles, as well as with 1,3-dipoles, were carried out to efficiently deliver N-CF 3 amidines/imidates/thioimidates and N-CF 3 azoles, demonstrating that they are a class of scalable NCF 3 -containing synthons in the synthesis of N-CF 3 compounds.

Controllable Regioselective [3+2] Cyclizations of N-CF3 Imidoyl Chlorides and Ph3PNNC: Divergent Synthesis of N-CF3 Triazoles

“…With the aim of expanding such a cyclization strategy, we focused on the development of a scalable alternative to N -CF 3 nitrilium salts. Just recently, N -CF 3 imidoyl chlorides were effectively synthesized for the first time in our lab, demonstrating their potential as efficient N -CF 3 nitrilium precursors. It is known that commercially available N -isocyaniminotriphenylphosphorane (Ph 3 PNNC or NIITP) has been widely applied as a 1,3-dipole in organic synthesis .…”