The double halofluorination reaction of alkynes using trihaloisocyanuric acids and Olah's reagent

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2023-11-01 DOI:10.1016/j.jfluchem.2023.110214
Hugo da S. Bragueroli, Pierre M. Esteves, Marcio C.S. de Mattos
{"title":"The double halofluorination reaction of alkynes using trihaloisocyanuric acids and Olah's reagent","authors":"Hugo da S. Bragueroli,&nbsp;Pierre M. Esteves,&nbsp;Marcio C.S. de Mattos","doi":"10.1016/j.jfluchem.2023.110214","DOIUrl":null,"url":null,"abstract":"<div><p>A simple and efficient method to produce a CF<sub>2</sub> group vicinal to a CX<sub>2</sub> group (X = chlorine or bromine) through double halofluorination reaction of alkynes using trihaloisocyanuric acid as halogenating agent and Pyridine.(HF)<sub>x</sub> (Olah's reagent) as fluoride source is presented. The alkynes used were 1-hexyne, 3-hexyne, phenylacetylene, 1-phenyl-1-butyne, and diphenylacetylene, obtaining, mainly, the desired products in 30–88 % yields. Among the trihaloisocyanuric acids studied, the tribromoisocyanuric acid gave the best yields and the most selective reactions, while trichloroisocyanuric acid, although the most reactive, had less selectivity in the reactions studied, giving in some cases several by-products.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"272 ","pages":"Article 110214"},"PeriodicalIF":1.7000,"publicationDate":"2023-11-01","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/S002211392300129X","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

A simple and efficient method to produce a CF2 group vicinal to a CX2 group (X = chlorine or bromine) through double halofluorination reaction of alkynes using trihaloisocyanuric acid as halogenating agent and Pyridine.(HF)x (Olah's reagent) as fluoride source is presented. The alkynes used were 1-hexyne, 3-hexyne, phenylacetylene, 1-phenyl-1-butyne, and diphenylacetylene, obtaining, mainly, the desired products in 30–88 % yields. Among the trihaloisocyanuric acids studied, the tribromoisocyanuric acid gave the best yields and the most selective reactions, while trichloroisocyanuric acid, although the most reactive, had less selectivity in the reactions studied, giving in some cases several by-products.

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
用三卤异氰尿酸和奥拉试剂进行炔烃的双卤代氟化反应
介绍了以三卤异氰尿酸为卤化剂,吡啶(HF) X (Olah试剂)为氟源,通过炔烃双卤代氟化反应生成与CX2 (X =氯或溴)相邻的CF2基团的简单高效方法。所使用的炔有1-己炔、3-己炔、苯乙炔、1-苯基-1-丁炔和二苯乙炔,产率主要在30 - 88%。在所研究的三卤异氰尿酸中,三溴异氰尿酸产率最好,反应选择性最强,而三氯异氰尿酸虽然反应性最强,但在所研究的反应中选择性较低,有时会产生几种副产物。
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