Iron‐Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion
Zan Chen, Quan Zhou, Qiao‐Lin Wang, Pu Chen, Biquan Xiong, Yun Liang, Kewen Tang, Yu Liu
Abstract
Abstract Iron‐mediated radical cyanoalkylsulfonylation/arylation of active olefins with cycloketone oxime derivatives via cleavage of C−C single bond and insertion of SO 2 is developed for the preparation of cyanoalkylsulfonylated oxindoles. This difunctionalization of carbon−carbon double bond via a radical pathway involves cyclobutanone oxime ester fragmentation, sulfonyl radical generation and radical addition/5‐ exo cyclization. The methodology displays good functional group tolerance and does not require any external bases or oxidants. magnified image
Topics & Concepts
ChemistryOximeSulfonylFunctional groupCyclobutanoneDouble bondMedicinal chemistrySulfurRadical cyclizationPhotochemistryOrganic chemistryRing (chemistry)AlkylPolymerSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions