可见光诱导可回收g-C3N4催化喹啉-2(1H)-酮的C-H / N-H交叉脱氢偶联胺化反应

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Zongjie Ma, Linzhao Li, Gaoli Chen, Cong Li, Taiping Gao
{"title":"可见光诱导可回收g-C3N4催化喹啉-2(1H)-酮的C-H / N-H交叉脱氢偶联胺化反应","authors":"Zongjie Ma,&nbsp;Linzhao Li,&nbsp;Gaoli Chen,&nbsp;Cong Li,&nbsp;Taiping Gao","doi":"10.1016/j.tet.2025.134707","DOIUrl":null,"url":null,"abstract":"<div><div>The development of efficient and sustainable methods for constructing carbon-nitrogen (C–N) bonds is of great importance in organic synthesis, particularly for the preparation of nitrogen-containing compounds with pharmaceutical relevance. Herein, a novel photocatalytic strategy utilizing sustainable graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) for the cross-dehydrogenative coupling (CDC) amination of quinoxalin-2(1<em>H</em>)-ones under visible light and mild conditions is described. Utilizing g-C<sub>3</sub>N<sub>4</sub> as a heterogeneous photocatalyst, a wide range of 3-aminoquinoxalin-2(1<em>H</em>)-one derivatives were synthesized in moderate to good yields (up to 89 %). The catalyst demonstrated remarkable stability and recyclability, maintaining its photocatalytic activity after five catalytic cycles. Mechanistic investigations indicated that the reaction follows a radical pathway. This method offers a green, sustainable alternative to metal-catalyzed CDC amination, with easy catalyst recovery showcasing g-C<sub>3</sub>N<sub>4</sub>'s potential as an eco-friendly photocatalyst.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"182 ","pages":"Article 134707"},"PeriodicalIF":2.1000,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible light-induced recyclable g-C3N4 catalyzed C–H/N–H cross-dehydrogenative coupling amination of Quinoxalin-2(1H)-ones\",\"authors\":\"Zongjie Ma,&nbsp;Linzhao Li,&nbsp;Gaoli Chen,&nbsp;Cong Li,&nbsp;Taiping Gao\",\"doi\":\"10.1016/j.tet.2025.134707\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The development of efficient and sustainable methods for constructing carbon-nitrogen (C–N) bonds is of great importance in organic synthesis, particularly for the preparation of nitrogen-containing compounds with pharmaceutical relevance. Herein, a novel photocatalytic strategy utilizing sustainable graphitic carbon nitride (g-C<sub>3</sub>N<sub>4</sub>) for the cross-dehydrogenative coupling (CDC) amination of quinoxalin-2(1<em>H</em>)-ones under visible light and mild conditions is described. Utilizing g-C<sub>3</sub>N<sub>4</sub> as a heterogeneous photocatalyst, a wide range of 3-aminoquinoxalin-2(1<em>H</em>)-one derivatives were synthesized in moderate to good yields (up to 89 %). The catalyst demonstrated remarkable stability and recyclability, maintaining its photocatalytic activity after five catalytic cycles. Mechanistic investigations indicated that the reaction follows a radical pathway. This method offers a green, sustainable alternative to metal-catalyzed CDC amination, with easy catalyst recovery showcasing g-C<sub>3</sub>N<sub>4</sub>'s potential as an eco-friendly photocatalyst.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"182 \",\"pages\":\"Article 134707\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2025-05-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402025002637\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025002637","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

开发高效、可持续的碳-氮(C-N)键构建方法在有机合成中具有重要意义,特别是在制备具有药物相关性的含氮化合物方面。本文描述了一种利用可持续氮化石墨碳(g-C3N4)在可见光和温和条件下进行喹诺沙林-2(1H)- 1交叉脱氢偶联胺化的新型光催化策略。利用g-C3N4作为非均相光催化剂,以中高收率(89%)合成了多种3-氨基喹啉-2(1H)- 1衍生物。该催化剂表现出良好的稳定性和可回收性,在5次催化循环后仍保持其光催化活性。机理研究表明,该反应遵循自由基途径。该方法为金属催化的CDC胺化提供了一种绿色、可持续的替代方法,催化剂易于回收,显示了g-C3N4作为环保光催化剂的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Visible light-induced recyclable g-C3N4 catalyzed C–H/N–H cross-dehydrogenative coupling amination of Quinoxalin-2(1H)-ones

Visible light-induced recyclable g-C3N4 catalyzed C–H/N–H cross-dehydrogenative coupling amination of Quinoxalin-2(1H)-ones
The development of efficient and sustainable methods for constructing carbon-nitrogen (C–N) bonds is of great importance in organic synthesis, particularly for the preparation of nitrogen-containing compounds with pharmaceutical relevance. Herein, a novel photocatalytic strategy utilizing sustainable graphitic carbon nitride (g-C3N4) for the cross-dehydrogenative coupling (CDC) amination of quinoxalin-2(1H)-ones under visible light and mild conditions is described. Utilizing g-C3N4 as a heterogeneous photocatalyst, a wide range of 3-aminoquinoxalin-2(1H)-one derivatives were synthesized in moderate to good yields (up to 89 %). The catalyst demonstrated remarkable stability and recyclability, maintaining its photocatalytic activity after five catalytic cycles. Mechanistic investigations indicated that the reaction follows a radical pathway. This method offers a green, sustainable alternative to metal-catalyzed CDC amination, with easy catalyst recovery showcasing g-C3N4's potential as an eco-friendly photocatalyst.
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
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
×
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