Selective Electrochemical Halogenation of Functionalized Quinolone
Meiqian Hu, Shuai Zhang, Changsheng Qin, Hongsheng Nie, Zhicheng Xiong, Xiaoyu Shi, Yumiao Zhao, Mingzhe Li, Shoucai Wang, Fanghua Ji, Guangbin Jiang
Abstract
This work describes an effective C3–H halogenation of quinoline-4(1 H )-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated quinoline-4(1 H )-ones with unique regioselectivity, broad substrate scope, and gram-scale synthesis employing convenient, environmentally friendly electrolysis, in an undivided cell. Mechanism studies have shown that halogen radicals can promote the activation of N–H bonds in quinolones.
Topics & Concepts
HalogenationQuinolineChemistryElectrolysisRegioselectivityCombinatorial chemistryQuinoloneElectrochemistryHalideHalogenSubstrate (aquarium)ElectrolyteOrganic chemistryAlkylBiochemistryPhysical chemistryElectrodeCatalysisAntibioticsGeologyOceanographyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques