电化学辅助弗里德兰德反应:一种高效、可持续的喹啉合成方法

IF 9.3 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Green Chemistry Pub Date : 2025-02-26 DOI:10.1039/d5gc00330j
Hamid Salehzadeh , Zahra Rostami Bigdeli , Kevin Lam
{"title":"电化学辅助弗里德兰德反应:一种高效、可持续的喹啉合成方法","authors":"Hamid Salehzadeh ,&nbsp;Zahra Rostami Bigdeli ,&nbsp;Kevin Lam","doi":"10.1039/d5gc00330j","DOIUrl":null,"url":null,"abstract":"<div><div>The Friedländer reaction is a well-established method for quinoline synthesis. However, it has significant limitations, including long reaction times, the use of environmentally harmful solvents and reagents, and significant waste generation. In this study, we present a simple, sustainable, efficient and one-step electrosynthetic strategy for the synthesis of quinolines from readily available nitro compounds using electric current. This reagent-free method operates under mild conditions with a constant-current electrolysis setup and achieves high conversion rates with excellent atom economy. Various substituted quinolines were successfully synthesised in good to excellent yields. In addition, cyclic voltammetry and controlled potential electrolysis studies were carried out to investigate the reaction mechanism of quinoline formation.</div></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"27 12","pages":"Pages 3346-3354"},"PeriodicalIF":9.3000,"publicationDate":"2025-02-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemically assisted Friedlander reaction: a highly efficient and sustainable method for quinoline synthesis†\",\"authors\":\"Hamid Salehzadeh ,&nbsp;Zahra Rostami Bigdeli ,&nbsp;Kevin Lam\",\"doi\":\"10.1039/d5gc00330j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The Friedländer reaction is a well-established method for quinoline synthesis. However, it has significant limitations, including long reaction times, the use of environmentally harmful solvents and reagents, and significant waste generation. In this study, we present a simple, sustainable, efficient and one-step electrosynthetic strategy for the synthesis of quinolines from readily available nitro compounds using electric current. This reagent-free method operates under mild conditions with a constant-current electrolysis setup and achieves high conversion rates with excellent atom economy. Various substituted quinolines were successfully synthesised in good to excellent yields. In addition, cyclic voltammetry and controlled potential electrolysis studies were carried out to investigate the reaction mechanism of quinoline formation.</div></div>\",\"PeriodicalId\":78,\"journal\":{\"name\":\"Green Chemistry\",\"volume\":\"27 12\",\"pages\":\"Pages 3346-3354\"},\"PeriodicalIF\":9.3000,\"publicationDate\":\"2025-02-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1463926225001499\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1463926225001499","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

Friedländer反应是一种公认的合成喹啉的方法。然而,它有很大的局限性,包括反应时间长,使用对环境有害的溶剂和试剂,以及产生大量废物。在这项研究中,我们提出了一种简单、可持续、高效的一步电合成策略,利用电流从现成的硝基化合物合成喹啉。这种无试剂的方法在温和的条件下使用恒流电解装置,并以优异的原子经济性实现高转化率。成功地合成了各种取代喹啉,收率很高。此外,通过循环伏安法和控制电位电解法研究了喹啉生成的反应机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Electrochemically assisted Friedlander reaction: a highly efficient and sustainable method for quinoline synthesis†

Electrochemically assisted Friedlander reaction: a highly efficient and sustainable method for quinoline synthesis†
The Friedländer reaction is a well-established method for quinoline synthesis. However, it has significant limitations, including long reaction times, the use of environmentally harmful solvents and reagents, and significant waste generation. In this study, we present a simple, sustainable, efficient and one-step electrosynthetic strategy for the synthesis of quinolines from readily available nitro compounds using electric current. This reagent-free method operates under mild conditions with a constant-current electrolysis setup and achieves high conversion rates with excellent atom economy. Various substituted quinolines were successfully synthesised in good to excellent yields. In addition, cyclic voltammetry and controlled potential electrolysis studies were carried out to investigate the reaction mechanism of quinoline formation.
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
Green Chemistry
Green Chemistry 化学-化学综合
CiteScore
16.10
自引率
7.10%
发文量
677
审稿时长
1.4 months
期刊介绍: Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
×
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