Visible-Light-Induced, Catalyst-Free Monofluoromethyl Sulfonylation of Alkenes with Iodine(III) Reagent and DABSO
Zhipeng Ye, Jingsong Yang, Sijia Yang, Meng Guo, Chu‐Ping Yuan, Yong-Qing Ye, Hong‐Bin Chen, Hao‐Yue Xiang, Kai Chen, Hua Yang
Abstract
A visible-light-induced radical relay strategy to access heterocycles bearing a monofluoromethylsufonyl moiety is reported, with PhI(OCOCH 2 F) 2 as the CH 2 F radical precursor and DABSO as the SO 2 source. A range of oxindoles, containing a CH 2 FSO 2 CH 2 – group at the C3 position, were synthesized from N -arylacrylamides in up to 97% yields. The protocol features catalyst-free photochemical tandem, mild reaction conditions, broad functional group compatibility, and good to excellent yields.
Topics & Concepts
ChemistryMoietyReagentCatalysisVisible spectrumFunctional groupTandemPhotochemistryIodineCombinatorial chemistryReaction conditionsOrganic chemistryPhysicsComposite materialOptoelectronicsPolymerMaterials scienceSulfur-Based Synthesis TechniquesFluorine in Organic ChemistryRadical Photochemical Reactions