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Synthesis of Polysubstituted Furans through Electrochemical Selenocyclization of Homopropargylic Alcohols

Debabrata Maiti, Atreyee Halder, Aswathy Sasidharan Pillai, Suman De Sarkar

2021The Journal of Organic Chemistry55 citationsDOI

Abstract

The current method represents an electrochemically driven synthetic route to access polysubstituted selenofuran derivatives through the diselenide-promoted cyclization of homopropargyl alcohols. The tandem electro-oxidative transformation operates at ambient temperature and in the absence of an external oxidant. This mild and efficient methodology exhibits good functional group compatibility, providing a broad range of substrate scopes up to 84% isolated yield. Further conversion of the seleno-functionality afforded other valuable furan derivatives.

Topics & Concepts

DiselenideFuranCombinatorial chemistryTandemCompatibility (geochemistry)Yield (engineering)ElectrochemistryChemistryFunctional groupOrganic chemistryMaterials scienceChemical engineeringEngineeringSeleniumPhysical chemistryElectrodePolymerComposite materialMetallurgySulfur-Based Synthesis TechniquesCatalytic Alkyne ReactionsOrganoselenium and organotellurium chemistry
Synthesis of Polysubstituted Furans through Electrochemical Selenocyclization of Homopropargylic Alcohols | Litcius