光氧化还原和铜双催化对缺电子烯烃的α-亲核加成。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-08-05 DOI:10.1021/acs.orglett.5c02573

Yuping Xiong, Zhiyi Zhou, Yahan Zhang*, Jian-Qiang Chen* and Jie Wu*,

{"title":"光氧化还原和铜双催化对缺电子烯烃的α-亲核加成。","authors":"Yuping Xiong, Zhiyi Zhou, Yahan Zhang*, Jian-Qiang Chen* and Jie Wu*, ","doi":"10.1021/acs.orglett.5c02573","DOIUrl":null,"url":null,"abstract":"Difunctionalization of olefins provides an efficient method for the construction of complex molecules. However, direct nucleophilic addition at the α-carbon of α,β-unsaturated olefins is relatively sluggish due to an electronic mismatch. Here, we report a synergetic photoredox/copper system to achieve sulfonylation of electron-deficient alkenes via a SO2-insertion strategy. With this approach, a wide range of sulfonyl-substituted lactone derivatives are synthesized under mild conditions with a broad substrate scope and good functional group compatibility.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 32","pages":"8915–8920"},"PeriodicalIF":5.0000,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Formal α-Nucleophilic Addition to Electron-Deficient Alkenes by Photoredox and Copper Dual Catalysis\",\"authors\":\"Yuping Xiong, Zhiyi Zhou, Yahan Zhang*, Jian-Qiang Chen* and Jie Wu*, \",\"doi\":\"10.1021/acs.orglett.5c02573\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Difunctionalization of olefins provides an efficient method for the construction of complex molecules. However, direct nucleophilic addition at the α-carbon of α,β-unsaturated olefins is relatively sluggish due to an electronic mismatch. Here, we report a synergetic photoredox/copper system to achieve sulfonylation of electron-deficient alkenes via a SO2-insertion strategy. With this approach, a wide range of sulfonyl-substituted lactone derivatives are synthesized under mild conditions with a broad substrate scope and good functional group compatibility.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 32\",\"pages\":\"8915–8920\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-08-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c02573\",\"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://pubs.acs.org/doi/10.1021/acs.orglett.5c02573","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

烯烃的双官能化为复杂分子的构造提供了一种有效的方法。然而，由于电子失配，α，β-不饱和烯烃的α-碳上的直接亲核加成反应相对缓慢。在这里，我们报道了一个协同光氧化还原/铜系统，通过so2插入策略实现缺电子烯烃的磺化。该方法在温和的条件下合成了种类繁多的磺酰取代内酯衍生物，具有广泛的底物范围和良好的官能团相容性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Formal α-Nucleophilic Addition to Electron-Deficient Alkenes by Photoredox and Copper Dual Catalysis

查看原文本刊更多论文

Formal α-Nucleophilic Addition to Electron-Deficient Alkenes by Photoredox and Copper Dual Catalysis

Difunctionalization of olefins provides an efficient method for the construction of complex molecules. However, direct nucleophilic addition at the α-carbon of α,β-unsaturated olefins is relatively sluggish due to an electronic mismatch. Here, we report a synergetic photoredox/copper system to achieve sulfonylation of electron-deficient alkenes via a SO₂-insertion strategy. With this approach, a wide range of sulfonyl-substituted lactone derivatives are synthesized under mild conditions with a broad substrate scope and good functional group compatibility.

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.