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Enantiocovergent Cross-Coupling Reaction with 1,4-Dihydropyridine Derivatives via Photoinduced Nickel Catalysis

Tongtong Li, Lifeng Luo, Xiaokai Cheng, Zhan Lu

2024ACS Catalysis20 citationsDOI

Abstract

Herein, we reported the enantioconvergent Csp 3 –Csp 2 cross-coupling reaction with 1,4-dihydropyridine (DHP) derivatives via photoredox/nickel dual catalysis to access chiral products with good yield and enantioselectivity. The operationally simple reaction was carried out under mild conditions with good functional group tolerance. Due to the use of a stoichiometric equivalent of aryl/alkenyl halides as coupling partners, the sequential and iterative synthesis could be achieved smoothly in one pot for the synthesis of position isomers and stereoisomers. In the proposed mechanism, kinetic experiments and mechanistic studies indicated that the radical generation, depended on the excited photocatalyst and DHP, was the rate-determining step.

Topics & Concepts

ChemistryCatalysisYield (engineering)Coupling reactionArylPhotoredox catalysisNickelCombinatorial chemistryHalideStoichiometryDihydropyridineFunctional groupPhotochemistryReaction mechanismPhotocatalysisOrganic chemistryAlkylMaterials scienceMetallurgyCalciumPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques