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Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-<i>a</i>]quinolines

Shouren Zhang, Jinwei Yuan, Guangchao Huang, Chengjia Ma, Jingjing Yang, Liangru Yang, Yongmei Xiao, Lingbo Qu

2023The Journal of Organic Chemistry15 citationsDOI

Abstract

A convenient and efficient visible-light-induced method has been developed for the construction of sulfonated and selenylated indolo[1,2- a ]quinolines through sulfonyl or selenyl radical-initiated tandem cyclization of unactivated alkynes with sodium sulfinates or diaryl diselenides under mild conditions. This protocol, which simply utilizes visible light as the safe and eco-friendly energy source and an inexpensive and nontoxic organic dye as a photocatalyst without the aid of an external photocatalyst, provides various sulfonyl- and selenyl-containing indolo[1,2- a ]quinolines in moderate to good yields.

Topics & Concepts

TandemSulfonylIntramolecular forceChemistryVisible spectrumCombinatorial chemistryPhotocatalysisPhotochemistryOrganic chemistryCatalysisMaterials scienceOptoelectronicsAlkylComposite materialSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions