无添加剂EDA光化学芳基化与三氟甲基苯并噻唑砜的三氟甲基化。

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC
Rui Lv, Lujun Lou, Tianshuai Zhu, Jing-Jing Zhang, Guang-Wei Wu*, Meng-Yang Hu*, Lijun Tang and Zhen Chen*, 
{"title":"无添加剂EDA光化学芳基化与三氟甲基苯并噻唑砜的三氟甲基化。","authors":"Rui Lv,&nbsp;Lujun Lou,&nbsp;Tianshuai Zhu,&nbsp;Jing-Jing Zhang,&nbsp;Guang-Wei Wu*,&nbsp;Meng-Yang Hu*,&nbsp;Lijun Tang and Zhen Chen*,&nbsp;","doi":"10.1021/acs.orglett.5c02330","DOIUrl":null,"url":null,"abstract":"<p >An additive-free trifluoromethylation–heteroarylation of enamides with trifluoromethyl heteroaryl sulfones via EDA photochemistry is reported. Under visible-light irradiation, diverse enamides and sulfones undergo efficient difunctionalization to afford CF<sub>3</sub>-heteroaryl amides in moderate to excellent yields, without the need for photocatalysts or additives. Mechanistic studies support the formation of a photoexcited EDA complex that triggers C–S bond cleavage, generating CF<sub>3</sub> and heteroaryl anions. This work provides a sustainable approach to alkene arylative difunctionalization and expands the utility of aryl sulfones in constructing CF<sub>3</sub>-containing scaffolds.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 31","pages":"8493–8498"},"PeriodicalIF":5.0000,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Additive-Free EDA Photochemical Arylative Trifluoromethylation of Enamides with Trifluoromethyl Benzothiazole Sulfones\",\"authors\":\"Rui Lv,&nbsp;Lujun Lou,&nbsp;Tianshuai Zhu,&nbsp;Jing-Jing Zhang,&nbsp;Guang-Wei Wu*,&nbsp;Meng-Yang Hu*,&nbsp;Lijun Tang and Zhen Chen*,&nbsp;\",\"doi\":\"10.1021/acs.orglett.5c02330\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >An additive-free trifluoromethylation–heteroarylation of enamides with trifluoromethyl heteroaryl sulfones via EDA photochemistry is reported. Under visible-light irradiation, diverse enamides and sulfones undergo efficient difunctionalization to afford CF<sub>3</sub>-heteroaryl amides in moderate to excellent yields, without the need for photocatalysts or additives. Mechanistic studies support the formation of a photoexcited EDA complex that triggers C–S bond cleavage, generating CF<sub>3</sub> and heteroaryl anions. This work provides a sustainable approach to alkene arylative difunctionalization and expands the utility of aryl sulfones in constructing CF<sub>3</sub>-containing scaffolds.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 31\",\"pages\":\"8493–8498\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-07-25\",\"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.5c02330\",\"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://pubs.acs.org/doi/10.1021/acs.orglett.5c02330","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

报道了用EDA光化学方法将烯酰胺与三氟甲基异芳基砜进行无添加剂三氟甲基异芳基化反应。在可见光照射下,不同的酰胺和砜发生有效的双官能化,在不需要光催化剂或添加剂的情况下,以中等至优异的收率获得cf3 -杂芳基酰胺。机理研究支持光激发EDA复合物的形成,该复合物触发C-S键裂解,生成CF3和杂芳基阴离子。本研究为烯烃芳基双功能化提供了一种可持续的方法,并扩展了芳基砜在构建含cf3支架中的应用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Additive-Free EDA Photochemical Arylative Trifluoromethylation of Enamides with Trifluoromethyl Benzothiazole Sulfones

Additive-Free EDA Photochemical Arylative Trifluoromethylation of Enamides with Trifluoromethyl Benzothiazole Sulfones

An additive-free trifluoromethylation–heteroarylation of enamides with trifluoromethyl heteroaryl sulfones via EDA photochemistry is reported. Under visible-light irradiation, diverse enamides and sulfones undergo efficient difunctionalization to afford CF3-heteroaryl amides in moderate to excellent yields, without the need for photocatalysts or additives. Mechanistic studies support the formation of a photoexcited EDA complex that triggers C–S bond cleavage, generating CF3 and heteroaryl anions. This work provides a sustainable approach to alkene arylative difunctionalization and expands the utility of aryl sulfones in constructing CF3-containing scaffolds.

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
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信