Regioselective Direct C–H Trifluoromethylation of Pyridine
Yang Xiao, Rui Sun, Shun Li, Xueli Zheng, Maolin Yuan, Bin Xu, Weidong Jiang, Hua Chen, Haiyan Fu, Ruixiang Li
Abstract
A highly efficient and regioselective direct C–H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent regioselectivity by treating the pyridinium iodide salts with trifluoroacetic acid in the presence of silver carbonate in N,N-dimethylformamide. The protocol features good functional group compatibility, easily available starting materials, and operational simplicity. Controlled experiments showed that the reaction may involve a nucleophilic trifluoromethylation mechanism.
Topics & Concepts
ChemistryTrifluoromethylationRegioselectivityPyridineCombinatorial chemistryStereochemistryComputational chemistryOrganic chemistryCatalysisTrifluoromethylAlkylFluorine in Organic ChemistryInorganic Fluorides and Related Compounds