O-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles

被引：0

作者：

Wei, Wenjie ^{[1
,2
]}

Xie, Qiangrong ^{[4
]}

Li, Xiaoyu ^{[2
]}

Xie, Yuanyuan ^{[1
,3
]}

Zhou, Hongwei ^{[2
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 341014, Peoples R China

[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Peoples R China

[3] Key Lab Pharmaceut Engn Zhejiang Prov, Hangzhou 310014, Peoples R China

[4] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310032, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2025年

基金：

中国国家自然科学基金;

关键词：

PROPARGYL-ALLENYL ISOMERIZATIONS; AROMATIC PUMMERER REACTION; METAL-FREE SYNTHESIS; EFFICIENT SYNTHESIS; POLYFUNCTIONALIZED BENZENES; SEQUENTIAL REACTIONS; SULFUR; CYCLOADDITION; CONSTRUCTION; DERIVATIVES;

D O I：

10.1039/d5ob00112a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indole scaffolds, which are important structural motifs in organic chemistry, have garnered sustained interest due to their prevalence in pharmaceuticals, agrochemicals, and natural products. This study establishes a novel umpolung activation strategy for gamma-position functionalization of electron-poor alkenyl sulfoxides, generating allylidenesulfonium intermediates that are subsequently trapped by indoles, achieving the synthesis of 3-functionalized indoles. Further transformations and plausible mechanism were investigated.

引用

页数：5

共 2 条

[1] Acylation of Electron-Poor Alkenyl Sulfoxides: Diverse Transformations for the Synthesis of Polysubstituted Phenols and Functionalized Carbocycles
Li, Xiaoyu
Zhang, Qianyun
Xie, Yuanyuan
Zhou, Hongwei
SYNTHESIS-STUTTGART, 2023, 55 (17): : 2674 - 2682
[2] Unprecedented Electron-Poor Octahedral Ta6 Clusters in a Solid-State Compound: Synthesis, Characterisations and Theoretical Investigations of Cs2BaTa6Br15O3
Demont, Antoine
Prestipino, Carmelo
Hernandez, Olivier
Elkaim, Erik
Paofai, Serge
Naumov, Nikolai
Fontaine, Bruno
Gautier, Regis
Cordier, Stephane
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (38) : 12711 - 12719

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