Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution
Tao Lei, Liang Ge, Yuanyuan Cheng, Bin Chen, Chen‐Ho Tung, Li‐Zhu Wu
Abstract
Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.
Topics & Concepts
EnamineChemistryCatalysisReactivity (psychology)HydrogenQuenching (fluorescence)PhosphorylationCombinatorial chemistryPhotochemistryOrganic chemistryBiochemistryMedicineAlternative medicinePathologyQuantum mechanicsPhysicsFluorescenceMetalloenzymes and iron-sulfur proteinsPorphyrin Metabolism and DisordersAsymmetric Hydrogenation and Catalysis