利用可见光进行非活化烯烃的无金属三氟甲基化/环化

IF 4.3 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemical Communications Pub Date : 2025-04-25 DOI:10.1039/d5cc01822f

Zhiping Yin, Xiaowen Qin, Chenwei Liu, Weiheng Yuan, Heng Li, Shuhui Sun, Tiefeng Xu

{"title":"利用可见光进行非活化烯烃的无金属三氟甲基化/环化","authors":"Zhiping Yin, Xiaowen Qin, Chenwei Liu, Weiheng Yuan, Heng Li, Shuhui Sun, Tiefeng Xu","doi":"10.1039/d5cc01822f","DOIUrl":null,"url":null,"abstract":"Visible light-driven radical trifluoromethylation/cyclization of unactivated alkenes offers a sustainable alternative to conventional methods for constructing chroman-4-one and related heterocyclic scaffolds. Herein, we report a metal-free photocatalytic system utilizing Rhodamine B as an organic photocatalyst and Togni II reagent as a trifluoromethyl source. This mild protocol enables efficient intramolecular tandem cyclization, affording diverse chroman-4-ones, dihydroquinolin-4-ones, and 1-indanones (24–69% yields) with broad functional group tolerance. The operational simplicity and avoidance of transition metals highlight the synthetic utility of this approach.","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"305 1","pages":""},"PeriodicalIF":4.3000,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Harnessing Visible Light for Metal-Free Trifluoromethylation/Cyclization of Unactivated Alkenes\",\"authors\":\"Zhiping Yin, Xiaowen Qin, Chenwei Liu, Weiheng Yuan, Heng Li, Shuhui Sun, Tiefeng Xu\",\"doi\":\"10.1039/d5cc01822f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Visible light-driven radical trifluoromethylation/cyclization of unactivated alkenes offers a sustainable alternative to conventional methods for constructing chroman-4-one and related heterocyclic scaffolds. Herein, we report a metal-free photocatalytic system utilizing Rhodamine B as an organic photocatalyst and Togni II reagent as a trifluoromethyl source. This mild protocol enables efficient intramolecular tandem cyclization, affording diverse chroman-4-ones, dihydroquinolin-4-ones, and 1-indanones (24–69% yields) with broad functional group tolerance. The operational simplicity and avoidance of transition metals highlight the synthetic utility of this approach.\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":\"305 1\",\"pages\":\"\"},\"PeriodicalIF\":4.3000,\"publicationDate\":\"2025-04-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5cc01822f\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5cc01822f","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

可见光驱动的非活化烯烃自由基三氟甲基化/环化为构建铬-4-酮及相关杂环支架提供了一种可持续的替代方法。本文报道了一种以罗丹明B为有机光催化剂，Togni II试剂为三氟甲基源的无金属光催化体系。这种温和的方案可以实现高效的分子内串联环化，提供不同的铬-4-酮、二氢喹啉-4-酮和1-吲哚酮（收率24-69%），具有广泛的官能团耐受性。操作简单和避免使用过渡金属突出了这种方法的综合效用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Harnessing Visible Light for Metal-Free Trifluoromethylation/Cyclization of Unactivated Alkenes

Visible light-driven radical trifluoromethylation/cyclization of unactivated alkenes offers a sustainable alternative to conventional methods for constructing chroman-4-one and related heterocyclic scaffolds. Herein, we report a metal-free photocatalytic system utilizing Rhodamine B as an organic photocatalyst and Togni II reagent as a trifluoromethyl source. This mild protocol enables efficient intramolecular tandem cyclization, affording diverse chroman-4-ones, dihydroquinolin-4-ones, and 1-indanones (24–69% yields) with broad functional group tolerance. The operational simplicity and avoidance of transition metals highlight the synthetic utility of this approach.

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

Chemical Communications 化学-化学综合

CiteScore

8.60

自引率

4.10%

发文量

2705

审稿时长

1.4 months

期刊介绍： ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.