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Organophotoredox-Catalyzed Sulfurization of Alkenes and Alkynes: Selective and Controlled Synthesis of Sulfoxides, β-Hydroxysulfoxides, and β-Keto Sulfides

Rajjakfur Rahaman, Md Tanjul Hoque, Dilip K. Maiti

2022Organic Letters20 citationsDOI

Abstract

A visible-light organophotoredox-catalyzed sulfurization of alkenes and alkynes with aromatic and heteroaromatic thiols using eco-friendly air (O 2 ) as the sole oxidant has been demonstrated. The established method delivers a novel, benign, and metal-free strategy for the difunctionalization of alkenes and alkynes using organophotoredox catalyst Eosin Y. The selective and controlled synthetic approach shows good substrate generality to afford sulfoxides, β-hydroxysulfoxides, and β-keto sulfides in high yield and excellent regioselectivity.

Topics & Concepts

ChemistryCatalysisRegioselectivityYield (engineering)Substrate (aquarium)Combinatorial chemistryEnvironmentally friendlyOrganic chemistryOceanographyMaterials scienceEcologyMetallurgyBiologyGeologySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsRadical Photochemical Reactions
Organophotoredox-Catalyzed Sulfurization of Alkenes and Alkynes: Selective and Controlled Synthesis of Sulfoxides, β-Hydroxysulfoxides, and β-Keto Sulfides | Litcius