硝基化合物和格氏试剂光催化合成芳胺的研究

IF 5.5 1区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Chen Yang, Tengfei Kang, Ya-Fei Wan, Tong Sun, Gang Li, Zhang-Jie Shi, Dong Xue
{"title":"硝基化合物和格氏试剂光催化合成芳胺的研究","authors":"Chen Yang,&nbsp;Tengfei Kang,&nbsp;Ya-Fei Wan,&nbsp;Tong Sun,&nbsp;Gang Li,&nbsp;Zhang-Jie Shi,&nbsp;Dong Xue","doi":"10.1002/cjoc.70029","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>Arylamines constitute a fundamental class of organic compounds critical to pharmaceuticals, dyes, and advanced materials. The direct synthesis of arylamines from nitro compounds demonstrates significant advantages in step economy, cost efficiency, and functional group compatibility. However, conventional methodologies frequently necessitate transition metal catalysts or excessive reducing agents, limiting their practical applicability. Herein, we introduce a highly efficient photochemical protocol for the synthesis of arylamines from readily accessible nitro compounds and Grignard reagents under purple light (390—395 nm) irradiation, eliminating the requirement for transition metal catalysts or external reducing agents. This protocol exhibits exceptional tolerance to sterically hindered substrates and sensitive functional groups. Preliminary mechanistic investigations suggest the involvement of nitrosoarenes and diarylamine nitrogen radicals as key intermediates in the reaction pathway.</p>\n <p>\n </p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 14","pages":"1679-1684"},"PeriodicalIF":5.5000,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Light-Promoted Synthesis of Arylamines from Nitro Compounds and Grignard Reagents\",\"authors\":\"Chen Yang,&nbsp;Tengfei Kang,&nbsp;Ya-Fei Wan,&nbsp;Tong Sun,&nbsp;Gang Li,&nbsp;Zhang-Jie Shi,&nbsp;Dong Xue\",\"doi\":\"10.1002/cjoc.70029\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>Arylamines constitute a fundamental class of organic compounds critical to pharmaceuticals, dyes, and advanced materials. The direct synthesis of arylamines from nitro compounds demonstrates significant advantages in step economy, cost efficiency, and functional group compatibility. However, conventional methodologies frequently necessitate transition metal catalysts or excessive reducing agents, limiting their practical applicability. Herein, we introduce a highly efficient photochemical protocol for the synthesis of arylamines from readily accessible nitro compounds and Grignard reagents under purple light (390—395 nm) irradiation, eliminating the requirement for transition metal catalysts or external reducing agents. This protocol exhibits exceptional tolerance to sterically hindered substrates and sensitive functional groups. Preliminary mechanistic investigations suggest the involvement of nitrosoarenes and diarylamine nitrogen radicals as key intermediates in the reaction pathway.</p>\\n <p>\\n </p>\\n </div>\",\"PeriodicalId\":151,\"journal\":{\"name\":\"Chinese Journal of Chemistry\",\"volume\":\"43 14\",\"pages\":\"1679-1684\"},\"PeriodicalIF\":5.5000,\"publicationDate\":\"2025-04-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70029\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70029","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

芳胺是一类基本的有机化合物,对药物、染料和先进材料至关重要。硝基化合物直接合成芳胺在步骤经济、成本效益和官能团相容性方面具有显著的优势。然而,传统的方法往往需要过渡金属催化剂或过多的还原剂,限制了它们的实际适用性。本文介绍了一种在紫外光(390-395 nm)照射下,由易于获得的硝基化合物和格氏试剂合成芳胺的高效光化学方法,消除了对过渡金属催化剂或外部还原剂的需求。该方案表现出对立体受阻底物和敏感官能团的特殊耐受性。初步的机制研究表明,亚硝基芳烃和二芳胺氮自由基参与了反应途径的关键中间体。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Light-Promoted Synthesis of Arylamines from Nitro Compounds and Grignard Reagents

Arylamines constitute a fundamental class of organic compounds critical to pharmaceuticals, dyes, and advanced materials. The direct synthesis of arylamines from nitro compounds demonstrates significant advantages in step economy, cost efficiency, and functional group compatibility. However, conventional methodologies frequently necessitate transition metal catalysts or excessive reducing agents, limiting their practical applicability. Herein, we introduce a highly efficient photochemical protocol for the synthesis of arylamines from readily accessible nitro compounds and Grignard reagents under purple light (390—395 nm) irradiation, eliminating the requirement for transition metal catalysts or external reducing agents. This protocol exhibits exceptional tolerance to sterically hindered substrates and sensitive functional groups. Preliminary mechanistic investigations suggest the involvement of nitrosoarenes and diarylamine nitrogen radicals as key intermediates in the reaction pathway.

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
Chinese Journal of Chemistry
Chinese Journal of Chemistry 化学-化学综合
CiteScore
8.80
自引率
14.80%
发文量
422
审稿时长
1.7 months
期刊介绍: The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.
×
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:604180095
Book学术官方微信