光激发硝基芳烃使非活化烯烃的1,2-/1,3-羟基三氟甲基化

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-09 DOI:10.1021/acs.orglett.4c04780

Cong Shi, Ruihua Liu, Zemin Wang, Chenxia Gao, Jia-Shu Chen, Hongyun Qin, Wenlong Shan, Wenli Zhuang, Nan Zhou, Xiangqian Li, Dayong Shi

{"title":"光激发硝基芳烃使非活化烯烃的1,2-/1,3-羟基三氟甲基化","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 CF3SO2Na.","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":"{\"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 CF3SO2Na.\",\"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}","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}

引用次数: 0

摘要

描述了非活化烯烃的1,2-/1,3-羟基三氟甲基化反应。该反应在温和和环境友好的条件下进行，没有光催化剂和金属催化剂，允许获得广泛的β-和γ-三氟甲基醇。初步的机理研究表明，该方案的实现依赖于光激发三重态硝基芳烃的双重功能，它作为氧原子源，使CF3SO2Na的单电子转移（SET）过程得以实现。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Anaerobic 1,2-/1,3-Hydroxytrifluoromethylation of Unactivated Alkenes Enabled by Photoexcited Nitroarenes

查看原文本刊更多论文

Anaerobic 1,2-/1,3-Hydroxytrifluoromethylation of Unactivated Alkenes Enabled by Photoexcited Nitroarenes

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

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.