Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles
Jingrui He, Aiyao Liu, Yingjie Yu, Chengting Wang, Haibo Mei, Jianlin Han
Abstract
An electrochemical sulfonylation-triggered cyclization reaction of indole-tethered terminal alkynes with sulfinates as sulfonyl sources has been developed, which affords exocyclic alkenyl tetrahydrocarbazoles in good chemical yields. This reaction features convenient operation and tolerates a wide scope of substrates with a variety of electronically and sterically diverse substituents. Furthermore, high E -stereoselectivity is observed for this reaction, which provides an efficient method for the preparation of functionalized tetrahydrocarbazole derivatives.
Topics & Concepts
Indole testAnnulationChemistrySulfonylSteric effectsStereoselectivityCombinatorial chemistryElectrochemistryStereochemistryOrganic chemistryCatalysisPhysical chemistryAlkylElectrodeSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods