镍（II）催化剂催化2-吡啶酮与氟烷基溴的区域选择性二氟烷基化

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-01-09 DOI:10.1002/asia.202401870

Chandini Pradhan, Disha Khandelwal, Prof. Dr. Benudhar Punji

{"title":"镍（II）催化剂催化2-吡啶酮与氟烷基溴的区域选择性二氟烷基化","authors":"Chandini Pradhan, Disha Khandelwal, Prof. Dr. Benudhar Punji","doi":"10.1002/asia.202401870","DOIUrl":null,"url":null,"abstract":"Regioselective C−H difluoroalkylation of diverse 2-pyridones with ethyl bromodifluoroacetates and bromodifluoroacetamides is accomplished by using a (dppf)NiCl2 catalyst under mild conditions. This efficient protocol could deliver a variety of C-3 difluoroalkylated pyridones with the tolerance of a range of highly susceptible functionalities, such as −Cl, −Br, −I, −COMe, −CN, −NMe2 and −NO2, including heteroarenes like pyridinyl, furanyl, thiophenyl and carbazolyl moieties. A preliminary mechanistic study suggests the radical pathway for the reaction involving fluoroalkyl radical intermediate.","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":"20 10","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Regioselective Difluoroalkylation of 2-Pyridones with Fluoroalkyl Bromides Enabled by a Nickel(II) Catalyst\",\"authors\":\"Chandini Pradhan, Disha Khandelwal, Prof. Dr. Benudhar Punji\",\"doi\":\"10.1002/asia.202401870\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Regioselective C−H difluoroalkylation of diverse 2-pyridones with ethyl bromodifluoroacetates and bromodifluoroacetamides is accomplished by using a (dppf)NiCl2 catalyst under mild conditions. This efficient protocol could deliver a variety of C-3 difluoroalkylated pyridones with the tolerance of a range of highly susceptible functionalities, such as −Cl, −Br, −I, −COMe, −CN, −NMe2 and −NO2, including heteroarenes like pyridinyl, furanyl, thiophenyl and carbazolyl moieties. A preliminary mechanistic study suggests the radical pathway for the reaction involving fluoroalkyl radical intermediate.\",\"PeriodicalId\":145,\"journal\":{\"name\":\"Chemistry - An Asian Journal\",\"volume\":\"20 10\",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-01-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry - An Asian Journal\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://aces.onlinelibrary.wiley.com/doi/10.1002/asia.202401870\",\"RegionNum\":3,\"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":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://aces.onlinelibrary.wiley.com/doi/10.1002/asia.202401870","RegionNum":3,"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

在温和条件下，使用（dppf）NiCl2催化剂，实现了多种2-吡啶酮与溴代氟乙酸乙酯和溴代氟乙酰胺的区域选择性C-H二氟烷基化。这种高效的方案可以提供多种C-3二氟烷基化吡啶酮，具有一系列高度敏感的功能，如-Cl、-Br、-I、-COMe、-CN、-NMe2和-NO2的耐受性，包括杂环芳烃，如吡啶基、呋喃基、噻吩基和咔唑基。初步的机理研究提出了含氟烷基自由基中间体反应的自由基途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Regioselective Difluoroalkylation of 2-Pyridones with Fluoroalkyl Bromides Enabled by a Nickel(II) Catalyst

查看原文本刊更多论文

Regioselective Difluoroalkylation of 2-Pyridones with Fluoroalkyl Bromides Enabled by a Nickel(II) Catalyst

Regioselective C−H difluoroalkylation of diverse 2-pyridones with ethyl bromodifluoroacetates and bromodifluoroacetamides is accomplished by using a (dppf)NiCl₂ catalyst under mild conditions. This efficient protocol could deliver a variety of C-3 difluoroalkylated pyridones with the tolerance of a range of highly susceptible functionalities, such as −Cl, −Br, −I, −COMe, −CN, −NMe₂ and −NO₂, including heteroarenes like pyridinyl, furanyl, thiophenyl and carbazolyl moieties. A preliminary mechanistic study suggests the radical pathway for the reaction involving fluoroalkyl radical intermediate.

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

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).