Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic <i>N</i>-Oxides
Dong Zhang, Jinlin Cai, Jinze Du, Qing‐Dong Wang, Jin‐Ming Yang, Rongqing Geng, Zheng Fang, Kai Guo
Abstract
An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.
Topics & Concepts
ChemistryIsoquinolineQuinolineMoietyElectrochemistryCombinatorial chemistryYield (engineering)Organic chemistryElectrodeMaterials scienceMetallurgyPhysical chemistryFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCatalytic C–H Functionalization Methods