{"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, Linzhao Li, Gaoli Chen, Cong Li, 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, Linzhao Li, Gaoli Chen, Cong Li, 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}
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.
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.