以8-氨基喹啉为导向基团的胺控制过渡金属催化氟芳烃的加氢脱氟和脱氟胺化。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-02 DOI:10.1021/acs.joc.5c00361

Anjun Ding,Xiaoyong Liu,Ziyue Xu,Shiyu Lei,Wen Liu,Jie Jiang,Shunxin Li,Zhengjiang Fu,Shengmei Guo,Hu Cai

{"title":"以8-氨基喹啉为导向基团的胺控制过渡金属催化氟芳烃的加氢脱氟和脱氟胺化。","authors":"Anjun Ding,Xiaoyong Liu,Ziyue Xu,Shiyu Lei,Wen Liu,Jie Jiang,Shunxin Li,Zhengjiang Fu,Shengmei Guo,Hu Cai","doi":"10.1021/acs.joc.5c00361","DOIUrl":null,"url":null,"abstract":"The selective defluorofunctionalization of fluoroarenes via transition-metal catalysis has garnered significant attention. This study presents an amine-controlled, directing-group-assisted strategy to achieve selective hydrodefluorination and defluoroamination of fluoroarenes. Dimethylamine enables the selective hydrodefluorination of fluoroarenes through β-hydride elimination from a nitro-centered nickel intermediate, while other amines furnish the defluoroamination reactions. In hydrodefluorination, dimethylformamide (DMF) serves a dual role as both the solvent and the source of dimethylamine. These reactions demonstrate high selectivity and a broad substrate scope.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Amine-Controlled, Transition-Metal-Catalyzed Hydrodefluorination and Defluoroamination of Fluoroarenes with 8-Aminoquinoline as a Directing Group.\",\"authors\":\"Anjun Ding,Xiaoyong Liu,Ziyue Xu,Shiyu Lei,Wen Liu,Jie Jiang,Shunxin Li,Zhengjiang Fu,Shengmei Guo,Hu Cai\",\"doi\":\"10.1021/acs.joc.5c00361\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The selective defluorofunctionalization of fluoroarenes via transition-metal catalysis has garnered significant attention. This study presents an amine-controlled, directing-group-assisted strategy to achieve selective hydrodefluorination and defluoroamination of fluoroarenes. Dimethylamine enables the selective hydrodefluorination of fluoroarenes through β-hydride elimination from a nitro-centered nickel intermediate, while other amines furnish the defluoroamination reactions. In hydrodefluorination, dimethylformamide (DMF) serves a dual role as both the solvent and the source of dimethylamine. These reactions demonstrate high selectivity and a broad substrate scope.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"19 1\",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-07-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.5c00361\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00361","RegionNum":2,"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

通过过渡金属催化的氟芳烃选择性去氟化引起了极大的关注。本研究提出了一种胺控制，定向基团辅助策略，以实现氟芳烃的选择性加氢脱氟和脱氟胺化。二甲胺通过消除以硝基为中心的镍中间体的β-氢化物，使氟芳烃选择性加氢脱氟，而其他胺则进行脱氟化反应。在加氢除氟过程中，二甲甲酰胺（DMF）既是溶剂又是二甲胺的来源，具有双重作用。这些反应表现出高选择性和广泛的底物范围。

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

Amine-Controlled, Transition-Metal-Catalyzed Hydrodefluorination and Defluoroamination of Fluoroarenes with 8-Aminoquinoline as a Directing Group.

The selective defluorofunctionalization of fluoroarenes via transition-metal catalysis has garnered significant attention. This study presents an amine-controlled, directing-group-assisted strategy to achieve selective hydrodefluorination and defluoroamination of fluoroarenes. Dimethylamine enables the selective hydrodefluorination of fluoroarenes through β-hydride elimination from a nitro-centered nickel intermediate, while other amines furnish the defluoroamination reactions. In hydrodefluorination, dimethylformamide (DMF) serves a dual role as both the solvent and the source of dimethylamine. These reactions demonstrate high selectivity and a broad substrate scope.

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

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.