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Visible Light Promoted Metal‐Free Sustainable Reduction of α‐Alkylidene Oxindoles/Succinimides

Anindita Bhowmick, Prakash K. Warghude, Ramakrishna G. Bhat

2022Asian Journal of Organic Chemistry10 citationsDOI

Abstract

Abstract Visible light promoted chemoselective metal free hydrogenation of activated double bond has been achieved via photoredox catalysis. Eosin Y has proved to be an efficient catalyst for the effective reduction of C−C double bonds of alkylidene oxindoles and succinimides under visible light. Commercially viable DIPEA has been employed as a sacrificial electron donor and it's in‐situ generated cationic radical acts as reductant in this transformation. The method proved to be practical as a broad range of substrates containing activated double bond were easily reduced. The method proved to be scalable on a gram quantity and the reduced product has been utilized successfully for the further synthetic application. The systematic and detailed mechanistic studies reveal the oxidative quenching of the photocatalyst by the activated double bond.

Topics & Concepts

ChemistrySuccinimidesDouble bondEosin YPhotoredox catalysisCatalysisPhotochemistryPhotocatalysisCationic polymerizationVisible spectrumQuenching (fluorescence)Combinatorial chemistryTandemOrganic chemistryFluorescenceOptoelectronicsMaterials sciencePhysicsQuantum mechanicsComposite materialRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods
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