Thianthrenation-promoted photoinduced alkene difunctionalization and aryl allylation with Morita–Baylis–Hillman adducts
Biplab Mondal, Ayan Chatterjee, Nitis Chandra Saha, Manoranjan Jana, Jaideep Saha
Abstract
An organophotoredox-catalyzed alkoxyallylation of feed-stock olefins, through thianthrenation using a Morita-Baylis-Hillman adduct as an allylating agent, is described. Site-selective addition of MeOH to an alkene-thianthrenium salt and its subsequent conversion into a nucleophilic radical species forms the basis of this unique difunctionalization strategy. The scope is also expanded into radical aryl allylation.
Topics & Concepts
AlkeneAdductArylChemistryBaylis–Hillman reactionMedicinal chemistryOrganic chemistryCatalysisAlkylSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions