Generation of copper fluoroalkyl complexes (CuRFLn) from chlorotrifluoroethylene and −RF transfer to aroyl chlorides

IF 1.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Luana L.T.N. Porto, Moutasem Seifi, Nicole Johnson, R. Baker
{"title":"Generation of copper fluoroalkyl complexes (CuRFLn) from chlorotrifluoroethylene and −RF transfer to aroyl chlorides","authors":"Luana L.T.N. Porto, Moutasem Seifi, Nicole Johnson, R. Baker","doi":"10.1139/cjc-2022-0240","DOIUrl":null,"url":null,"abstract":"Given the importance of fluorinated drugs and agrochemicals, fluoroalkylation of organic electrophiles that can be performed at a late stage of chemical synthesis has attracted a flurry of contributions. New fluoroalkyl groups can be obtained by insertion of fluoroalkenes into Cu–H bonds. Chlorotrifluoroethylene undergoes regioselective insertion in its reaction with Stryker's reagent, [CuH(PPh3)]6 and triphos to give [Cu(CFClCF2H)(μ−κ1,κ2-triphos)]2, which mediates the fluoroalkylation of several aroyl chlorides (triphos = bis(2-diphenylphosphinoethyl)-phenylphosphine). In contrast, attempted −RF transfer to aryl iodides instead affords aryl–aryl coupling products.","PeriodicalId":9420,"journal":{"name":"Canadian Journal of Chemistry","volume":"1 1","pages":""},"PeriodicalIF":1.1000,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Canadian Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1139/cjc-2022-0240","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

Given the importance of fluorinated drugs and agrochemicals, fluoroalkylation of organic electrophiles that can be performed at a late stage of chemical synthesis has attracted a flurry of contributions. New fluoroalkyl groups can be obtained by insertion of fluoroalkenes into Cu–H bonds. Chlorotrifluoroethylene undergoes regioselective insertion in its reaction with Stryker's reagent, [CuH(PPh3)]6 and triphos to give [Cu(CFClCF2H)(μ−κ1,κ2-triphos)]2, which mediates the fluoroalkylation of several aroyl chlorides (triphos = bis(2-diphenylphosphinoethyl)-phenylphosphine). In contrast, attempted −RF transfer to aryl iodides instead affords aryl–aryl coupling products.
从三氟乙烯和- RF转移到芳酰氯生成氟烷基铜配合物(CuRFLn)
考虑到氟化药物和农用化学品的重要性,有机亲电试剂的氟烷基化可以在化学合成的后期阶段进行,这吸引了大量的贡献。通过在Cu-H键上插入氟烯烃可以得到新的氟烷基。三氟氯乙烯与Stryker试剂[CuH(PPh3)]6和三磷酸发生区域选择性插入反应,得到[Cu(CFClCF2H)(μ−κ1,κ2-三磷酸)]2,介导了几种芳酰氯(三磷酸=双(2-二苯基膦乙基)-苯基膦)的氟烷基化反应。相反,尝试- RF转移到芳基碘化物反而提供芳基-芳基偶联产物。
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 求助全文
来源期刊
Canadian Journal of Chemistry
Canadian Journal of Chemistry 化学-化学综合
CiteScore
1.90
自引率
9.10%
发文量
99
审稿时长
1 months
期刊介绍: Published since 1929, the Canadian Journal of Chemistry reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Articles describing original research are welcomed.
×
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