Copper-Catalyzed Synthesis of Quinoline-4-thiols from Diaryliodonium Salts, Alkynyl Sulfides, and Nitriles
Shun-Qin Chang, Donghui Xing, Yuzhen Zheng, Liangbin Huang
Abstract
A three-component cascade cyclization catalyzed by copper was employed to synthesize quinoline-4-thiols using easily available diaryliodonium salts, alkynyl sulfides, and nitriles as starting materials. Sulfur atoms play an important role in controlling the regioselectivity, by stabilizing the high-valent vinyl copper intermediate. Meanwhile, the sulfide group at position 4 of quinoline could be further utilized as a transformable group for ipso -transformation and as a directing group for C–H functionalization, affording various multifunctional quinoline derivatives.
Topics & Concepts
QuinolineChemistryRegioselectivityCatalysisSulfurCopperSulfideCombinatorial chemistrySurface modificationFunctional groupOrganic chemistryPhysical chemistryPolymerSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions