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Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction

Fu‐Sheng He, Yanfang Yao, Zhimei Tang, Yanjie Qiu, Wenlin Xie, Jie Wu

2021Chemical Communications32 citationsDOI

Abstract

and diselenides has been developed. This method enables the rapid assembly of β-cyanoalkylsulfonylated vinyl selenides in moderate to good yields. Advantages of this protocol include a broad substrate scope, good functional group tolerance and the late-stage functionalization of complex molecules. Moreover, the potential utility of this methodology is demonstrated through simple oxidation of the products to access synthetically important alkynyl sulfones. Mechanistic studies suggest that a cyanoalkylsulfonyl radical intermediate is involved in this process.

Topics & Concepts

DABCOChemistryFunctional groupOximeCombinatorial chemistrySubstrate (aquarium)Surface modificationMoleculeCatalysisComponent (thermodynamics)Organic chemistryPolymerGeologyOceanographyThermodynamicsPhysicsPhysical chemistrySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryChemical Synthesis and Reactions