Synthesis of <i>N</i>-CF<sub>3</sub> Amidines/Imidates/Thioimidates <i>via</i> <i>N</i>-CF<sub>3</sub> Nitrilium Ions
Ru Zhong Zhang, Wanqiao Huang, Ru Xue Zhang, Cong Xu, Mang Wang
Abstract
An efficient methodology for the synthesis of a wide range of N-CF3 imidic acid derivatives is presented. In this reaction, N-CF3 nitrilium ions were generated via N-trifluoromethylation of nitriles using PhICF3Cl under catalysis with DMAP, followed by the capture of N-, O-, or S-centered nucleophiles to give diverse N-CF3 amidines, imidates, and thioimidates. The method provides a platform for preparing N-CF3 compounds with potential applications.
Topics & Concepts
TrifluoromethylationChemistryNucleophileIonCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryTrifluoromethylAlkylFluorine in Organic ChemistrySynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms