{"title":"Redox-Neutral Decarboxylative and Desulfonylative C(sp<sup>3</sup>) Trifluoromethylation: Method Development and Mechanistic Inquiry.","authors":"Chris M Seong, Courtney C Roberts","doi":"10.1021/acs.joc.3c00872","DOIUrl":null,"url":null,"abstract":"<p><p>Sodium triflinate (CF<sub>3</sub>SO<sub>2</sub>Na) is an inexpensive bench-stable radical CF<sub>3</sub> source that is often activated by external oxidants such as peroxides. However, despite the commercial accessibility of CF<sub>3</sub>SO<sub>2</sub>Na, the salt has never been applied to decarboxylative trifluoromethylation due to challenges in controlled cross-radical coupling. We report a redox-neutral approach to decarboxylative C(sp<sup>3</sup>) trifluoromethylation of carboxylic acid derivatives. Mechanistic inquiry is performed to address the limitations in scope.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":" ","pages":"16114-16120"},"PeriodicalIF":3.3000,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"88","ListUrlMain":"https://doi.org/10.1021/acs.joc.3c00872","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2023/7/19 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Sodium triflinate (CF3SO2Na) is an inexpensive bench-stable radical CF3 source that is often activated by external oxidants such as peroxides. However, despite the commercial accessibility of CF3SO2Na, the salt has never been applied to decarboxylative trifluoromethylation due to challenges in controlled cross-radical coupling. We report a redox-neutral approach to decarboxylative C(sp3) trifluoromethylation of carboxylic acid derivatives. Mechanistic inquiry is performed to address the limitations in scope.
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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