Visible-Light Copper Catalysis for the Synthesis of α-Alkyl-Acetophenones by the Radical-Type Ring Opening of Sulfonium Salts and Oxidative Alkylation of Alkenes
Xuan Li, Xufeng Li, Wenwen Cui, Qilong Wu, Linyuan Wang, Jian Lv, Daoshan Yang
Abstract
Direct difunctionalization of simple alkenes has been treated as a powerful synthetic strategy for the construction of highly functionalized skeletons. In this study, direct oxidative coupling of sulfonium salts with alkenes was achieved under mild conditions by a blue-light-driven photoredox process using a copper complex as a photosensitizer. This protocol allows regioselective synthesis of aryl/alkyl ketones from simple sulfonium salts and aromatic alkenes via selective C-S bond cleavage of sulfonium salts and oxidative alkylation of aromatic alkenes using dimethyl sulfoxide (DMSO) as a mild oxidant.
Topics & Concepts
ChemistrySulfoniumAlkylationAlkylRegioselectivityArylPhotoredox catalysisOrganic chemistryOxidative coupling of methanePhotochemistryBond cleavageCatalysisCombinatorial chemistryMedicinal chemistryPhotocatalysisSalt (chemistry)Sulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods