Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2023-10-01 DOI:10.1016/j.jfluchem.2023.110187
Scott T. Iacono , Nathan J. Weeks , Dennis W. Smith Jr.
{"title":"Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest","authors":"Scott T. Iacono ,&nbsp;Nathan J. Weeks ,&nbsp;Dennis W. Smith Jr.","doi":"10.1016/j.jfluchem.2023.110187","DOIUrl":null,"url":null,"abstract":"<div><p>The nature of the structural configuration of fluorinated ethers has been widespread as a crucial component for improving high performance polymers, industrial agrochemicals, and targets for important pharmaceutical drugs. This is a result of countless advances in organo-fluorine methodologies with this unique substructure in order to overcome many traditional synthetic challenges. In this work, we expand on the preparation of fluorinated ethers by introducing hetero-nucleophiles to a highly electrophilic aryl trifluorovinyl ether affording a new class of difunctional aryl/alkyl fluorinated ethers that would serve as useful intermediates. The facile reaction chemistry of various nucleophile substrates, effect of base concerning regio-selectivity, and structural elucidation trends of the synthesized aryl/alkyl fluoroethers will be discussed.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"271 ","pages":"Article 110187"},"PeriodicalIF":1.7000,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Fluorine Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022113923001021","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0

Abstract

The nature of the structural configuration of fluorinated ethers has been widespread as a crucial component for improving high performance polymers, industrial agrochemicals, and targets for important pharmaceutical drugs. This is a result of countless advances in organo-fluorine methodologies with this unique substructure in order to overcome many traditional synthetic challenges. In this work, we expand on the preparation of fluorinated ethers by introducing hetero-nucleophiles to a highly electrophilic aryl trifluorovinyl ether affording a new class of difunctional aryl/alkyl fluorinated ethers that would serve as useful intermediates. The facile reaction chemistry of various nucleophile substrates, effect of base concerning regio-selectivity, and structural elucidation trends of the synthesized aryl/alkyl fluoroethers will be discussed.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
亲核试剂加在1-溴-4-(三氟乙烯氧基)苯上的系统研究:合成感兴趣的氟化醚的通用中间体
氟化醚结构构型的性质已被广泛认为是改进高性能聚合物、工业农用化学品和重要药物靶标的关键组成部分。这是有机氟方法的无数进步的结果,具有这种独特的亚结构,以克服许多传统的合成挑战。在这项工作中,我们通过在高度亲电的芳基三氟乙烯醚中引入异亲核试剂来扩展氟化醚的制备,从而提供了一类新的双官能芳基/烷基氟化醚,可作为有用的中间体。讨论了各种亲核底物的易反应化学,碱对区域选择性的影响,以及合成的芳烷基氟醚的结构解析趋势。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Journal of Fluorine Chemistry
Journal of Fluorine Chemistry 化学-无机化学与核化学
CiteScore
3.80
自引率
10.50%
发文量
99
审稿时长
33 days
期刊介绍: The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.
期刊最新文献
Controlled nucleophilic aromatic substitution of hexafluorobenzene using a flow microreactor Oligoacrylates with perfluoroalkyl substituents based on hexafluoropropylene trimer as environment friendly hydrophobic coatings Corrosion of iron in liquid uranium hexafluoride at 80 °C. Part I: Normal and abnormal experimental kinetics 6-Polyfluoroalkyl-1-arylhexane-1,3,5-triones: Syntheses, ring-chain tautomerism and dehydrative cyclization to 6-polyfluoroalkyl-1-arylpyran-4H-ones FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1