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Dual Cobalt and Photoredox Catalysis Enabled Intermolecular Oxidative Hydrofunctionalization

Han‐Li Sun, Fan Yang, Wei-Ting Ye, Jun‐Jie Wang, Rong Zhu

2020ACS Catalysis107 citationsDOI

Abstract

A general protocol has been developed for the Markovnikov-selective intermolecular hydrofunctionalization based on visible-light-mediated Co/Ru dual catalysis. The key feature involves the photochemical oxidation of an organocobalt(III) intermediate derived from hydrogen atom transfer, which is supported by electrochemical analysis, quenching studies, and stoichiometric experiments. This redox process enables the efficient branch-selective alkylation of pharmaceutically important nucleophiles (phenols, sulfonamides, and various N-heterocycles) using a wide range of alkenes including moderately electron-deficient ones. Moreover, light-gated polar functionalization via organocobalt species was demonstrated.

Topics & Concepts

ChemistryPhotoredox catalysisCatalysisPhotochemistryIntermolecular forceNucleophileQuenching (fluorescence)RedoxCobaltCombinatorial chemistryElectron transferAlkylationRegioselectivityPhotocatalysisOrganic chemistryMoleculeQuantum mechanicsFluorescencePhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Dual Cobalt and Photoredox Catalysis Enabled Intermolecular Oxidative Hydrofunctionalization | Litcius