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Catalytic Electrophilic Thiocarbocyclization of Allenes

Quanbin Jiang, Huimin Li, Xiaodan Zhao

2021Organic Letters17 citationsDOI

Abstract

An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence of TMSOTf. Not only electrophilic arylthio reagents but also electrophilic alkylthio reagents worked well under these conditions. Furthermore, the method could be applied to intermolecular azidothiolation of allenes.

Topics & Concepts

ElectrophileChemistryReagentCatalysisIndeneSelenideIntermolecular forceElectrophilic additionCombinatorial chemistryOrganic chemistryMoleculeSeleniumSulfur-Based Synthesis TechniquesCyberloafing and Workplace BehaviorChemical Synthesis and Reactions
Catalytic Electrophilic Thiocarbocyclization of Allenes | Litcius