{"title":"Facile Preparation of SeCF3-substituted Alkenes from Alkenyl Iodides and Selenium Powder","authors":"Haruka Matsui, Yuki Kojima, Koji Hirano","doi":"10.1093/chemle/upae076","DOIUrl":null,"url":null,"abstract":"\n A synthetic method of SeCF3-substituted alkenes by a copper-mediated trifluoromethylselenolation of alkenyl iodides has been developed. In the presence of CuI and bpy, AgSeCF3 generated in-situ from Ag salt, TMSCF3, and commercially available Se powder, can be successfully coupled with alkenyl iodides to produce the trifluoromethylselenoalkenes with high chemoselectivity. The reaction shows a broad substrate scope including alkenyl iodides derived from biologically active molecules. Moreover, the feasibility of its scale-up synthesis has been demonstrated, thereby underscoring the practicality of the protocol.","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":" 781","pages":""},"PeriodicalIF":17.7000,"publicationDate":"2024-04-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1093/chemle/upae076","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A synthetic method of SeCF3-substituted alkenes by a copper-mediated trifluoromethylselenolation of alkenyl iodides has been developed. In the presence of CuI and bpy, AgSeCF3 generated in-situ from Ag salt, TMSCF3, and commercially available Se powder, can be successfully coupled with alkenyl iodides to produce the trifluoromethylselenoalkenes with high chemoselectivity. The reaction shows a broad substrate scope including alkenyl iodides derived from biologically active molecules. Moreover, the feasibility of its scale-up synthesis has been demonstrated, thereby underscoring the practicality of the protocol.
通过铜介导的烯基碘化物三氟甲基硒化反应，开发了一种 SeCF3 取代烯的合成方法。在 CuI 和 bpy 的存在下，由 Ag 盐、TMSCF3 和市售 Se 粉末原位生成的 AgSeCF3 可以成功地与烯基碘化物偶联，以高化学选择性生成三氟甲基硒烯烃。该反应的底物范围很广，包括来自生物活性分子的烯基碘化物。此外，该反应还证明了放大合成的可行性，从而突出了该方案的实用性。
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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