Ruthenium Catalyzed Mechanochemical Transformation of Sulfonamide Group to Fluoro, Trifluoromethyl, and Trifluoromethoxy Functionalities.

IF 3.5 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Satenik Mkrtchyan, Vishal B Purohit, Vaibhav D Prajapati, Ronak V Prajapati, Oleksandr Shalimov, Sehrish Sarfaraz, Khurshid Ayub, Viktor O Iaroshenko
{"title":"Ruthenium Catalyzed Mechanochemical Transformation of Sulfonamide Group to Fluoro, Trifluoromethyl, and Trifluoromethoxy Functionalities.","authors":"Satenik Mkrtchyan, Vishal B Purohit, Vaibhav D Prajapati, Ronak V Prajapati, Oleksandr Shalimov, Sehrish Sarfaraz, Khurshid Ayub, Viktor O Iaroshenko","doi":"10.1002/asia.202500221","DOIUrl":null,"url":null,"abstract":"<p><p>A convenient route for the mechanochemical synthesis of fluorinated aromatic compounds, that is, fluoro, trifluoromethyl, and trifluoromethoxy arenes, has been developed via pyrylium tetrafluoroborate (Pyry-BF<sub>4</sub>)-mediated desulfonamidative cross-coupling of primary sulfonamides under the synergy of a piezoelectric material BaTiO<sub>3</sub>, and Ru-catalysis. This is the first-ever report on the selective transformation of sulfonamide (SO<sub>2</sub>NH<sub>2</sub>) functionality to CF<sub>3</sub>/OCF<sub>3</sub>/F group in a single step under mechanochemical ball-milling conditions. Considering the importance of primary sulfonamides as the valuable pharmacophores, the present desulfonamidative cross-coupling approach could have potential to get synthetic utility in pharmaceutical industries for the late-stage functionalization of sulfonamide drugs and related active pharmaceutical ingredients (APIs).</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202500221"},"PeriodicalIF":3.5000,"publicationDate":"2025-04-09","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://doi.org/10.1002/asia.202500221","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

Abstract

A convenient route for the mechanochemical synthesis of fluorinated aromatic compounds, that is, fluoro, trifluoromethyl, and trifluoromethoxy arenes, has been developed via pyrylium tetrafluoroborate (Pyry-BF4)-mediated desulfonamidative cross-coupling of primary sulfonamides under the synergy of a piezoelectric material BaTiO3, and Ru-catalysis. This is the first-ever report on the selective transformation of sulfonamide (SO2NH2) functionality to CF3/OCF3/F group in a single step under mechanochemical ball-milling conditions. Considering the importance of primary sulfonamides as the valuable pharmacophores, the present desulfonamidative cross-coupling approach could have potential to get synthetic utility in pharmaceutical industries for the late-stage functionalization of sulfonamide drugs and related active pharmaceutical ingredients (APIs).

求助全文
约1分钟内获得全文 求助全文
来源期刊
Chemistry - An Asian Journal
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).
×
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:481959085
Book学术官方微信