{"title":"Anaerobic 1,2-/1,3-Hydroxytrifluoromethylation of Unactivated Alkenes Enabled by Photoexcited Nitroarenes","authors":"Cong Shi, Ruihua Liu, Zemin Wang, Chenxia Gao, Jia-Shu Chen, Hongyun Qin, Wenlong Shan, Wenli Zhuang, Nan Zhou, Xiangqian Li, Dayong Shi","doi":"10.1021/acs.orglett.4c04780","DOIUrl":null,"url":null,"abstract":"An anaerobic 1,2-/1,3-hydroxytrifluoromethylation of unactivated alkenes is described. This reaction proceeds in mild and environmentally friendly conditions without photocatalyst and metal catalyst, allowing access to a wide range of β- and γ-trifluoromethyl alcohols. Preliminary mechanistic investigations indicate that the accomplishment of this protocol relies on the dual functionality of the photoexcited triplet nitroarenes, which serve as the oxygen atom source and enable the single-electron transfer (SET) process with CF<sub>3</sub>SO<sub>2</sub>Na.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-01-09","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.4c04780","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
An anaerobic 1,2-/1,3-hydroxytrifluoromethylation of unactivated alkenes is described. This reaction proceeds in mild and environmentally friendly conditions without photocatalyst and metal catalyst, allowing access to a wide range of β- and γ-trifluoromethyl alcohols. Preliminary mechanistic investigations indicate that the accomplishment of this protocol relies on the dual functionality of the photoexcited triplet nitroarenes, which serve as the oxygen atom source and enable the single-electron transfer (SET) process with CF3SO2Na.
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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