General Synthesis of <i>N</i>-CF<sub>3</sub> Heteroaryl Amides via Successive Fluorination and Acylation of Sterically Hindered Isothiocyanates
Min Tao, Jiasheng Qian, Zuanguang Chen, Lin‐Kun An, David M. Wilson, J. Liu
Abstract
We report the one-pot synthesis of N -CF 3 heteroaryl amides (NTFMHA) from heteroaryl carboxylic acids and sterically hindered isothiocyanates, including various amino acid analogues, in the presence of AgF. The key to this reaction is the utilization of free heteroaryl acyl chlorides, rather than their corresponding hydrochloride salts. This method represents a complementary method of our previous work and enables modification to a variety of previously inaccessible structures, including α-tertiary amines and N -CF 3 -modified pharmaceuticals.
Topics & Concepts
Steric effectsAcylationChemistryHydrochloridePrimary (astronomy)Organic chemistryStereochemistryCombinatorial chemistryCatalysisPhysicsAstronomyFluorine in Organic ChemistryChemical Synthesis and AnalysisSynthesis and Catalytic Reactions