Regioselective Access to Substituted Benzothiophenes/furans through Electrochemical Selenium-Promoted Skeletal Rearrangement
Debabrata Maiti, Atreyee Halder, Aritri Saha, Suman De Sarkar
Abstract
An electrochemical strategy for the regioselective construction of seleno-benzothiophenes/furans is reported through electrochemical selenocyclization, followed by Wagner-Meerwein rearrangement. This electro-oxidative tandem process operates under metal-free and external chemical oxidant-free conditions. Advantageously, unprotected homopropargyl alcohols were found to be compatible under the reaction conditions, releasing water and dihydrogen as the biproduct. This methodology reveals good functional group tolerance, allowing a broad spectrum of substrate scopes of up to 87% isolated yield.
Topics & Concepts
RegioselectivityChemistryElectrochemistryTandemYield (engineering)Combinatorial chemistrySubstrate (aquarium)SeleniumFunctional groupOrganic chemistryCatalysisElectrodeGeologyMaterials scienceMetallurgyOceanographyPhysical chemistryPolymerComposite materialSulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryRadical Photochemical Reactions