β-硫酰胺砜使铜催化环丙烯开环/磺化：获得烷基芳基砜

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-09 DOI:10.1021/acs.orglett.4c04352

Arshad Ali, Cherry Chung, Jingru Wang, Lang Liu, Yi Kong, Chongyuan Wang, Yidong Liu, Qin Yin, Shaoquan Lin

{"title":"β-硫酰胺砜使铜催化环丙烯开环/磺化：获得烷基芳基砜","authors":"Arshad Ali, Cherry Chung, Jingru Wang, Lang Liu, Yi Kong, Chongyuan Wang, Yidong Liu, Qin Yin, Shaoquan Lin","doi":"10.1021/acs.orglett.4c04352","DOIUrl":null,"url":null,"abstract":"Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing compounds has thus attracted considerable attention. Here, we introduce a protocol for the preparation of alkyl aryl sulfones under mild conditions. This protocol employs β-thioamide sulfone as a novel sulfone motif donor. It forms sulfinates in situ under basic conditions, which then undergo cross-coupling with the intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones\",\"authors\":\"Arshad Ali, Cherry Chung, Jingru Wang, Lang Liu, Yi Kong, Chongyuan Wang, Yidong Liu, Qin Yin, Shaoquan Lin\",\"doi\":\"10.1021/acs.orglett.4c04352\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing compounds has thus attracted considerable attention. Here, we introduce a protocol for the preparation of alkyl aryl sulfones under mild conditions. This protocol employs β-thioamide sulfone as a novel sulfone motif donor. It forms sulfinates in situ under basic conditions, which then undergo cross-coupling with the intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"24 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-01-09\",\"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.4c04352\",\"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.4c04352","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

砜基序在生物活性化合物和功能材料中发挥着重要作用。因此，开发构建含磺酰化合物的有效方法引起了相当大的注意。本文介绍了一种在温和条件下制备烷基芳基砜的方法。该方案采用β-硫酰胺砜作为新的砜基序供体。它在基本条件下原位形成亚硫酸盐，然后与无配体铜催化环丙烯（cpe）开环生成的中间体发生交叉偶联。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

查看原文本刊更多论文

β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing compounds has thus attracted considerable attention. Here, we introduce a protocol for the preparation of alkyl aryl sulfones under mild conditions. This protocol employs β-thioamide sulfone as a novel sulfone motif donor. It forms sulfinates in situ under basic conditions, which then undergo cross-coupling with the intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

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.