离子对有机催化介导的 3-硝基杂环烯烃与烯丙基砜的异构 (3 + 2) 环加成反应

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-08 DOI:10.1021/acs.orglett.5c00215

Léo Birbaum, Moussa Ndiaye, Mahmoud Hachem, Stéphane Perrio, Michael De Paolis, Isabelle Chataigner

{"title":"离子对有机催化介导的 3-硝基杂环烯烃与烯丙基砜的异构 (3 + 2) 环加成反应","authors":"Léo Birbaum, Moussa Ndiaye, Mahmoud Hachem, Stéphane Perrio, Michael De Paolis, Isabelle Chataigner","doi":"10.1021/acs.orglett.5c00215","DOIUrl":null,"url":null,"abstract":"We report the first example of dearomative (3 + 2) cycloadditions of 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in the presence of allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, and efficient protocol for the synthesis of functionalized 2,3-fused cyclopentannulated indolines and dihydrobenzofurans.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Dearomative (3 + 2) Cycloadditions of 3-Nitroheteroarenes with Allenyl Sulfones Mediated by Ion Pair Organocatalysis\",\"authors\":\"Léo Birbaum, Moussa Ndiaye, Mahmoud Hachem, Stéphane Perrio, Michael De Paolis, Isabelle Chataigner\",\"doi\":\"10.1021/acs.orglett.5c00215\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"We report the first example of dearomative (3 + 2) cycloadditions of 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in the presence of allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, and efficient protocol for the synthesis of functionalized 2,3-fused cyclopentannulated indolines and dihydrobenzofurans.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"29 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2025-02-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c00215\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00215","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Dearomative (3 + 2) Cycloadditions of 3-Nitroheteroarenes with Allenyl Sulfones Mediated by Ion Pair Organocatalysis

查看原文本刊更多论文

Dearomative (3 + 2) Cycloadditions of 3-Nitroheteroarenes with Allenyl Sulfones Mediated by Ion Pair Organocatalysis

We report the first example of dearomative (3 + 2) cycloadditions of 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in the presence of allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, and efficient protocol for the synthesis of functionalized 2,3-fused cyclopentannulated indolines and dihydrobenzofurans.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.