钯催化的 1-芳基吡啶 N-氧化物电化学碘化反应

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-02-27 DOI:10.1021/acs.joc.3c0260110.1021/acs.joc.3c02601
Hang Zhou, Masahiro Miyasaka, Yu-Han Wang, Takuya Kochi and Fumitoshi Kakiuchi*, 
{"title":"钯催化的 1-芳基吡啶 N-氧化物电化学碘化反应","authors":"Hang Zhou,&nbsp;Masahiro Miyasaka,&nbsp;Yu-Han Wang,&nbsp;Takuya Kochi and Fumitoshi Kakiuchi*,&nbsp;","doi":"10.1021/acs.joc.3c0260110.1021/acs.joc.3c02601","DOIUrl":null,"url":null,"abstract":"<p >The palladium-catalyzed C–H iodination of 1-arylpyridine <i>N</i>-oxides proceeded under electrochemical oxidation conditions using I<sub>2</sub> as an iodine source. The reaction of isoquinoline <i>N</i>-oxides possessing various <i>para</i>- or <i>meta</i>-substituted aryl groups at the 1-position proceeded to give the corresponding iodination products. Electron-donating groups on the aryl group facilitated the reaction to give relatively high yields of the product. The reaction was also found to be applicable to 2-aryl-3-picoline <i>N</i>-oxides.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16300–16306 16300–16306"},"PeriodicalIF":3.3000,"publicationDate":"2024-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Electrochemical Iodination of 1-Arylpyridine N-Oxides\",\"authors\":\"Hang Zhou,&nbsp;Masahiro Miyasaka,&nbsp;Yu-Han Wang,&nbsp;Takuya Kochi and Fumitoshi Kakiuchi*,&nbsp;\",\"doi\":\"10.1021/acs.joc.3c0260110.1021/acs.joc.3c02601\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The palladium-catalyzed C–H iodination of 1-arylpyridine <i>N</i>-oxides proceeded under electrochemical oxidation conditions using I<sub>2</sub> as an iodine source. The reaction of isoquinoline <i>N</i>-oxides possessing various <i>para</i>- or <i>meta</i>-substituted aryl groups at the 1-position proceeded to give the corresponding iodination products. Electron-donating groups on the aryl group facilitated the reaction to give relatively high yields of the product. The reaction was also found to be applicable to 2-aryl-3-picoline <i>N</i>-oxides.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":\"89 22\",\"pages\":\"16300–16306 16300–16306\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-02-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.3c02601\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.3c02601","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

在电化学氧化条件下,以 I2 为碘源,钯催化了 1-芳基吡啶 N-氧化物的 C-H 碘化反应。1 位上具有各种对位或偏取代芳基的异喹啉 N-氧化物在反应过程中生成了相应的碘化产物。芳基上的电子供能基团促进了反应的进行,从而得到相对较高产率的产物。该反应还适用于 2-芳基-3-甲基吡啶 N-氧化物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

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
Palladium-Catalyzed Electrochemical Iodination of 1-Arylpyridine N-Oxides

The palladium-catalyzed C–H iodination of 1-arylpyridine N-oxides proceeded under electrochemical oxidation conditions using I2 as an iodine source. The reaction of isoquinoline N-oxides possessing various para- or meta-substituted aryl groups at the 1-position proceeded to give the corresponding iodination products. Electron-donating groups on the aryl group facilitated the reaction to give relatively high yields of the product. The reaction was also found to be applicable to 2-aryl-3-picoline N-oxides.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
期刊最新文献
Rhodium(III)-Catalyzed Regioselective C4 Alkylation of Indoles with Nitroalkenes Stoichiometry Dependence in the Consecutive, Competing Reduction, Halogenation, or Deoxygenation of Aryl Carbonyls Synthesis of Rapicone Based on Acyl Ketene–Alkyne Cycloaddition Molecular Dynamics of the Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction. Protecting Group Control of Hydroxyketone-Hemiketal Tautomeric Equilibrium Enables the Stereoselective Synthesis of a 1'-Azido C-Nucleoside.
×
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