N-Trifluoroethoxy Benzotriazolium Triflate：用于烯烃直接自由基三氟乙氧基化的现成试剂

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-29 DOI:10.1021/acs.orglett.4c0371010.1021/acs.orglett.4c03710

Mingxi Chen, Yuhui Lu, Yiwen Shen and Quande Wang*,

{"title":"N-Trifluoroethoxy Benzotriazolium Triflate：用于烯烃直接自由基三氟乙氧基化的现成试剂","authors":"Mingxi Chen, Yuhui Lu, Yiwen Shen and Quande Wang*, ","doi":"10.1021/acs.orglett.4c0371010.1021/acs.orglett.4c03710","DOIUrl":null,"url":null,"abstract":"Herein, we describe the development and application of a novel benzotriazole-based reagent toward radical trifluoroethoxylation. Various alkene classes, including styrene derivatives, enol carbonates, and allyl silanes, are viable reaction partners in this transformation, yielding diverse trifluoroethoxylated products. Furthermore, this method is readily applicable for the late-stage modification of natural product and drugs molecules. Mechanistic and computational studies suggest the intermediacy of an OCH2CF3 radical generated under photocatalytic conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 44","pages":"9586–9591 9586–9591"},"PeriodicalIF":4.9000,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"N-Trifluoroethoxy Benzotriazolium Triflate: A Readily Available Reagent for Direct Radical Trifluoroethoxylation of Alkenes\",\"authors\":\"Mingxi Chen, Yuhui Lu, Yiwen Shen and Quande Wang*, \",\"doi\":\"10.1021/acs.orglett.4c0371010.1021/acs.orglett.4c03710\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we describe the development and application of a novel benzotriazole-based reagent toward radical trifluoroethoxylation. Various alkene classes, including styrene derivatives, enol carbonates, and allyl silanes, are viable reaction partners in this transformation, yielding diverse trifluoroethoxylated products. Furthermore, this method is readily applicable for the late-stage modification of natural product and drugs molecules. Mechanistic and computational studies suggest the intermediacy of an OCH2CF3 radical generated under photocatalytic conditions.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"26 44\",\"pages\":\"9586–9591 9586–9591\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-10-29\",\"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.4c03710\",\"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.4c03710","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

在此，我们介绍了一种新型苯并三唑基试剂在自由基三氟乙氧基化方面的开发和应用。包括苯乙烯衍生物、烯醇碳酸酯和烯丙基硅烷在内的各种烯类都是这种转化过程中可行的反应伙伴，可产生多种三氟乙氧基化产物。此外，这种方法还可用于天然产品和药物分子的后期改性。机理和计算研究表明，在光催化条件下生成的 OCH2CF3 自由基是中间产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

N-Trifluoroethoxy Benzotriazolium Triflate: A Readily Available Reagent for Direct Radical Trifluoroethoxylation of Alkenes

Herein, we describe the development and application of a novel benzotriazole-based reagent toward radical trifluoroethoxylation. Various alkene classes, including styrene derivatives, enol carbonates, and allyl silanes, are viable reaction partners in this transformation, yielding diverse trifluoroethoxylated products. Furthermore, this method is readily applicable for the late-stage modification of natural product and drugs molecules. Mechanistic and computational studies suggest the intermediacy of an OCH₂CF₃ radical generated under photocatalytic conditions.

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.