Electrochemical <scp>C3</scp>‐Thiocyanation of Quinolines
Ziyun Wang, R. Shi, Jialing Zhang, Lin‐Bao Zhang, Li‐Rong Wen, Weisi Guo
Abstract
Comprehensive Summary The site‐selective C–H thiocyanation of quinoline has potential application value but remains undeveloped. We report herein an electrochemical C3‐thiocyanation of quinoline derivatives under external oxidant‐free conditions. The key to success for this reaction is the in situ formation of activated silylquinolinium salts. This method exhibits mild reaction conditions, broad substrate scope, and excellent site‐selectivity. The practicality of this protocol is further demonstrated by a scale‐up reaction, follow‐up transformations, and late‐stage thiocyanation of quinoline‐based bioactive molecules.
Topics & Concepts
ChemistryQuinolineCombinatorial chemistryElectrochemistrySubstrate (aquarium)Reaction conditionsSelectivityOrganic chemistryCatalysisElectrodeOceanographyPhysical chemistryGeologySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions