Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle–Kirmse reaction
Fu‐Yuan Yang, Tian‐Jiao Han, Shi‐Kun Jia, Min‐Can Wang, Guang‐Jian Mei
Abstract
The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence of a carbenoid intermediate, this protocol represents the first non-carbenoid variant of the Doyle-Kirmse reaction. Under mild conditions, a variety of tertiary thioethers have been readily prepared in good to excellent yields.
Topics & Concepts
CarbenoidSulfoniumSigmatropic reactionCatalysisChemistryMedicinal chemistryPhotochemistryStereochemistryOrganic chemistrySalt (chemistry)RhodiumSulfur-Based Synthesis TechniquesCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods