Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins
Xin Li, Weili Si, Zhanhui Liu, Haitao Qian, Tingxue Wang, Shengnan Leng, Jinwei Sun, Yan Jiao, Xuan Zhang
Abstract
Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp3)–C(sp3) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor–acceptor complex. This protocol for the conversion of a C–OH bond to a C–C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.
Topics & Concepts
ChemistryAlkylAlkylationOlefin fiberAlcoholPhotocatalysisSalt (chemistry)Photoredox catalysisPhotochemistrySurface modificationOrganic chemistryMedicinal chemistryCatalysisPhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods