Electrochemical Amination of Aryl Halides with NH3

Yaowen Liu, Yanfei Sun, Yuan Deng, Youai Qiu
{"title":"Electrochemical Amination of Aryl Halides with NH3","authors":"Yaowen Liu,&nbsp;Yanfei Sun,&nbsp;Yuan Deng,&nbsp;Youai Qiu","doi":"10.1002/ange.202504459","DOIUrl":null,"url":null,"abstract":"<p>Primary arylamines are the most pivotal class of organic motifs in pharmaceuticals, agrochemicals, ligands and natural products. Ammonia (NH<sub>3</sub>) is an ideal nitrogen source in terms of reactivity, atom economy, and environmental compatibility. Despite significant progress in the synthesis of primary arylamines, the development of a general method for rapid access to diversely functionalized primary arylamines is still urgent and necessary. Herein, we developed a method for the direct synthesis of primary arylamines through electrochemical amination of aryl halides with NH<sub>3</sub>. Notably, the weak nucleophilic reagent NH<sub>3</sub> was directly used as an ammonia surrogate, allowing for efficient conversion of carbon-halogen bonds to diverse primary arylamines with good functional group tolerance. A broad scope of functionalized primary arylamines has been achieved in moderate to excellent yields.</p>","PeriodicalId":7803,"journal":{"name":"Angewandte Chemie","volume":"137 24","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ange.202504459","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

Primary arylamines are the most pivotal class of organic motifs in pharmaceuticals, agrochemicals, ligands and natural products. Ammonia (NH3) is an ideal nitrogen source in terms of reactivity, atom economy, and environmental compatibility. Despite significant progress in the synthesis of primary arylamines, the development of a general method for rapid access to diversely functionalized primary arylamines is still urgent and necessary. Herein, we developed a method for the direct synthesis of primary arylamines through electrochemical amination of aryl halides with NH3. Notably, the weak nucleophilic reagent NH3 was directly used as an ammonia surrogate, allowing for efficient conversion of carbon-halogen bonds to diverse primary arylamines with good functional group tolerance. A broad scope of functionalized primary arylamines has been achieved in moderate to excellent yields.

芳基卤化物的NH3电化学胺化
伯芳胺是医药、农用化学品、配体和天然产物中最重要的一类有机基序。氨(NH3)在反应性、原子经济性和环境相容性方面是一种理想的氮源。尽管伯芳胺的合成取得了重大进展,但开发一种快速获取多种功能化伯芳胺的通用方法仍然是迫切和必要的。在此,我们开发了一种用NH3将芳基卤化物电化学胺化直接合成伯芳胺的方法。值得注意的是,弱亲核试剂NH3被直接用作氨替代物,允许碳卤素键有效地转化为各种具有良好官能团耐受性的伯芳胺。广泛的功能化伯芳胺已经实现了中等到优异的产量。
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
Angewandte Chemie
Angewandte Chemie 化学科学, 有机化学, 有机合成
自引率
0.00%
发文量
0
审稿时长
1 months
×
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