{"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, Lujun Lou, Tianshuai Zhu, Jing-Jing Zhang, Guang-Wei Wu*, Meng-Yang Hu*, Lijun Tang and Zhen Chen*, ","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, Lujun Lou, Tianshuai Zhu, Jing-Jing Zhang, Guang-Wei Wu*, Meng-Yang Hu*, Lijun Tang and Zhen Chen*, \",\"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}
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.
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.