Visible-light-induced photocatalytic iododi(per)fluoroalkylation of 5-amino-N-allyl-1,2,3-triazole-4-carboxamides

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2024-04-24 DOI:10.1016/j.jfluchem.2024.110292
Ivanna Yu. Danyliuk , Sergiy V. Kemskyi , Vladyslav M. Polishchuk , Svitlana V. Shishkina , Mykhailo V. Vovk
{"title":"Visible-light-induced photocatalytic iododi(per)fluoroalkylation of 5-amino-N-allyl-1,2,3-triazole-4-carboxamides","authors":"Ivanna Yu. Danyliuk ,&nbsp;Sergiy V. Kemskyi ,&nbsp;Vladyslav M. Polishchuk ,&nbsp;Svitlana V. Shishkina ,&nbsp;Mykhailo V. Vovk","doi":"10.1016/j.jfluchem.2024.110292","DOIUrl":null,"url":null,"abstract":"<div><p>Readily available di(per)fluoroalkyl iodides and ethyl difluoroiodoacetate have been efficiently reacted with 5-amino-<em>N</em>-allyl-1,2,3-triazole-4-carboxamides in the presence of DIPEA under visible-light induction and fluorescein catalysis to produce high yields of the corresponding adducts, <em>N</em>-(<em>n</em>-propyl) carboxamides vicinally difunctionalized with the iodine atom and the di(per)fluoroalkyl or (methoxycarbonyl)difluoromethyl moiety. As shown experimentally, this regiospecific and triazole amino group tolerant reaction involves a radical process.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-04-24","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/S0022113924000526","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

Readily available di(per)fluoroalkyl iodides and ethyl difluoroiodoacetate have been efficiently reacted with 5-amino-N-allyl-1,2,3-triazole-4-carboxamides in the presence of DIPEA under visible-light induction and fluorescein catalysis to produce high yields of the corresponding adducts, N-(n-propyl) carboxamides vicinally difunctionalized with the iodine atom and the di(per)fluoroalkyl or (methoxycarbonyl)difluoromethyl moiety. As shown experimentally, this regiospecific and triazole amino group tolerant reaction involves a radical process.

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
可见光诱导的 5-氨基-N-烯丙基-1,2,3-三唑-4-甲酰胺碘(过)氟烷基化光催化反应
在可见光诱导和荧光素催化下,现成的二(全)氟烷基碘化物和二氟碘乙酸乙酯与 5-氨基-N-烯丙基-1,2,3-三唑-4-甲酰胺在 DIPEA 存在下发生了高效反应,生成了高产率的相应加合物、N-(正丙基)羧酰胺与碘原子和二(全)氟烷基或(甲氧羰基)二氟甲基发生代双官能化反应。实验表明,这种具有区域特异性和三唑氨基耐受性的反应涉及一个自由基过程。
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
Electrochemical radiofluorination using a split-bipolar electrode Morphological control of bicontinuous phase-separated patterns by preparing mixed monolayers using non-amphiphilic s-triazine derivatives with three fluorinated chains Dimerization of perfluoropropyl vinyl ether during the pyrolysis of hexafluoropropylene oxide dimer Recent advances in fluorine chemistry using flow technology Hydrothermal transformations of hydrated cerium(IV) fluoride in NaOH or HF media. The first crystal structure in the cerium tetrafluoride hydrate family
×
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