<i>N</i>-CF<sub>3</sub> Imidoyl Chlorides: Scalable <i>N</i>-CF<sub>3</sub> Nitrilium Precursors for the Construction of <i>N</i>-CF<sub>3</sub> Compounds
Ru Zhong Zhang, Yan Fang Gao, Jian Xin Yu, Cong Xu, Mang Wang
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.
Topics & Concepts
SynthonChemistryNucleophileTrifluoromethylationMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisTrifluoromethylAlkylFluorine in Organic ChemistryInorganic Fluorides and Related Compounds