Tunable Redox‐Neutral Photocatalysis: Visible Light‐Induced Arylperfluoroalkylation of Alkenes Regulated by Protons
Yuan Li, Yuan Li, Xin Zhang, Deqiang Liang, Yanni Li, Yanni Li, Shulin Gao, Xiangguang Li, Ying Dong, Baoling Wang, Yinhai Ma
Abstract
Abstract A redox entanglement in photoredox catalysis is discovered and discussed. Using MeOH as a proton source and Eosin Y as a photocatalyst, a problematic and redox‐neutral perfluoroalkylation/cyclization cascade of alkenes with perfluoroalkyl iodides can be streamlined, furnishing perfluoroalkylated indolines, indoles, dihydroisoquinolinones, and indolin‐2‐ones with a good functional‐group tolerance under base‐, metal‐, and redox‐agent‐free conditions. Mechanistic investigations revealed that MeOH does not activate the perfluoroalkyl C−I bond, but rather enhances the oxidation part of the photocatalytic cycle.
Topics & Concepts
ChemistryRedoxPhotocatalysisPhotochemistryCatalysisEosin YProtonPhotoredox catalysisOrganocatalysisCombinatorial chemistryOrganic chemistryEnantioselective synthesisPhysicsQuantum mechanicsFluorine in Organic ChemistryRadical Photochemical ReactionsOxidative Organic Chemistry Reactions