Lewis Acid-Catalyzed Formal [4 + 2] Reaction of Alkynyl Sulfides and 2-Pyrones To Access Polysubstituted Aryl Sulfides
Bin Huang, Donghui Xing, Huanfeng Jiang, Liangbin Huang
Abstract
A practical and efficient method to access polysubstituted aryl sulfides has been discovered via a Lewis acid-catalyzed reaction between alkynyl sulfide and 2-pyrone, involving a Diels-Alder/retro-Diels-Alder pathway. Alkynyl sulfide as an electron-rich dienophile and 2-pyrones as electron-poor dienes are conjunctively transformed into a series of polysubstituted aryl sulfides with broad functional group compatibility in good to excellent yields (40 examples, 43-88% yield). The robustness and practicality of the protocol has been demonstrated through gram-scale synthesis and the ease of transformation of the resulting products.
Topics & Concepts
ChemistryArylSulfideCatalysisLewis acids and basesCombinatorial chemistryOrganic chemistryAlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions