{"title":"O-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles†","authors":"Wenjie Wei , Qiangrong Xie , Xiaoyu Li , Yuanyuan Xie , Hongwei Zhou","doi":"10.1039/d5ob00112a","DOIUrl":null,"url":null,"abstract":"<div><div>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 γ-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.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 16","pages":"Pages 3937-3941"},"PeriodicalIF":2.7000,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025002174","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/25 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
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 γ-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.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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