{"title":"Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/N-Acyloxyphthalimide-Assisted Decarboxylation Sequence","authors":"Fei Huang, Yunquan Man and Bo Xu*, ","doi":"10.1021/acs.orglett.5c0060110.1021/acs.orglett.5c00601","DOIUrl":null,"url":null,"abstract":"<p >We have developed a metal-free approach for synthesizing <i>E</i>-trifluoromethylated alkenes from readily available aldehydes and the <i>N</i>-hydroxyphtalimide ester of trifluoropropionic acid. To address the challenge of defluorination, we conducted high-throughput screening of reaction conditions. We discovered that acid–base co-catalysis effectively suppresses defluorination, thereby enhancing product yields. A key advantage of our method is its reliance on inexpensive, commercially available starting materials and straightforward reaction conditions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 15","pages":"3889–3892 3889–3892"},"PeriodicalIF":4.9000,"publicationDate":"2025-04-09","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.5c00601","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
We have developed a metal-free approach for synthesizing E-trifluoromethylated alkenes from readily available aldehydes and the N-hydroxyphtalimide ester of trifluoropropionic acid. To address the challenge of defluorination, we conducted high-throughput screening of reaction conditions. We discovered that acid–base co-catalysis effectively suppresses defluorination, thereby enhancing product yields. A key advantage of our method is its reliance on inexpensive, commercially available starting materials and straightforward reaction conditions.
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.