{"title":"Polyfluoroalkanoic Acids as Fluoroalkylating Reagents: Strategy for Direct Access to Rf-Embedded Amides","authors":"Lalit Mohan Kabadwal, Shuvojit Haldar, Atanu Bera, Debasis Banerjee","doi":"10.1021/acs.orglett.4c04418","DOIUrl":null,"url":null,"abstract":"Herein, we have reported the application of bench stable perfluoroalkanoic acids as fluoro-alkylating reagents in combination with DIB and primary amides for sequential one-pot transformation to R<sub>f</sub>-embedded functionalized amides under metal-free conditions. The protocol is tolerant to a range of sensitive functional groups (>33 examples and up to 90% yield), and perfluoro acids. Preliminary mechanistic studies, control experiments, in situ <sup>19</sup>F-NMR analyses, and the synthesis of intermediate species were performed to understand the reaction pathways.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"351 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-01-02","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.4c04418","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
Abstract
Herein, we have reported the application of bench stable perfluoroalkanoic acids as fluoro-alkylating reagents in combination with DIB and primary amides for sequential one-pot transformation to Rf-embedded functionalized amides under metal-free conditions. The protocol is tolerant to a range of sensitive functional groups (>33 examples and up to 90% yield), and perfluoro acids. Preliminary mechanistic studies, control experiments, in situ 19F-NMR analyses, and the synthesis of intermediate species were performed to understand the reaction pathways.
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.
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