Visible-Light-Driven Radical Multicomponent Reaction of 2-Vinylanilines, Sulfonyl Chlorides, and Sulfur Ylides for Synthesis of Indolines
Visible-Light-Driven Radical Multicomponent Reaction of 2-Vinylanilines, Sulfonyl Chlorides, and Sulfur Ylides for Synthesis of Indolines
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2 乙烯基苯胺、磺酰氯和硫叶立德的可见光驱动自由基多组分反应合成二氢吲哚
DOI：
10.1021/acs.orglett.0c00602
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Jia-Rong Chen
中科院分区：
文献类型：
--
作者：
Mukund M. D. Pramanik;Fan Yuan;Dong-Mei Yan;Wen-Jing Xiao;Jia-Rong Chen
报道了一种可见光驱动的光氧化还原催化2-乙烯基苯胺、磺酰氯和硫叶立德的多组分反应。该方案具有氧化还原中性的温和条件，广泛的底物范围和良好的官能团耐受性，提供了各种磺化2，3-二取代吲哚啉的途径。该产物可以通过选择性芳构化/亲核取代过程转化为各种各样的官能化吲哚。机理研究表明，磺酰氯和硫叶立德作为自由基源，和反应进行通过顺序的自由基加成/加成/热SN 2-取代过程。
A visible-light-driven photoredox-catalyzed multicomponent reaction of 2-vinylanilines, sulfonyl chlorides, and sulfur ylides is described. This protocol features redox-neutral mild conditions, a broad substrate scope, and good functional group tolerance, providing access to various sulfonated 2,3-disubstituted indolines. The product can be transformed to a diverse range of functionalized indoles by a selective aromatization/nucleophilic substitution process. Mechanistic investigations suggest that both sulfonyl chlorides and sulfur ylides serve as radical sources, and the reaction proceeds through a sequential radical addition/addition/thermal SN2-substitution process.