Yanchun Lin , Xi Zhou , Yixuan Zheng , Bingran Chen , Yang Liu , Yi Zhang , Qiongjiao Yan , Wei Wang , Fener Chen
{"title":"可见光促进喹喔啉-2(1H)-酮或香豆素与烷氧基丙烯酰氯的 C3-H 烷氧基羰基化反应。","authors":"Yanchun Lin , Xi Zhou , Yixuan Zheng , Bingran Chen , Yang Liu , Yi Zhang , Qiongjiao Yan , Wei Wang , Fener Chen","doi":"10.1039/d4ob01525h","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we describe a green and efficient photoredox catalytic C3–H alkoxycarbonylation between quinoxalin-2(1<em>H</em>)-ones or coumarins and readily available alkyloxalyl chlorides under ambient conditions. A series of quinoxaline-3-carbonyl and coumarin-3-carbonyl compounds are prepared through the radical addition of <em>in situ</em>-generated alkoxycarbonyl radicals. Notably, this protocol features mild conditions, operational simplicity, and excellent functional group tolerance. More importantly, the carboxylated products can be readily derivatized into other important compounds that would be of great potential for the exploitation of pharmaceutically active compounds.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 43","pages":"Pages 8591-8595"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible light-promoted C3–H alkoxycarbonylation of quinoxalin-2(1H)-ones or coumarins with alkyloxalyl chlorides†\",\"authors\":\"Yanchun Lin , Xi Zhou , Yixuan Zheng , Bingran Chen , Yang Liu , Yi Zhang , Qiongjiao Yan , Wei Wang , Fener Chen\",\"doi\":\"10.1039/d4ob01525h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we describe a green and efficient photoredox catalytic C3–H alkoxycarbonylation between quinoxalin-2(1<em>H</em>)-ones or coumarins and readily available alkyloxalyl chlorides under ambient conditions. A series of quinoxaline-3-carbonyl and coumarin-3-carbonyl compounds are prepared through the radical addition of <em>in situ</em>-generated alkoxycarbonyl radicals. Notably, this protocol features mild conditions, operational simplicity, and excellent functional group tolerance. More importantly, the carboxylated products can be readily derivatized into other important compounds that would be of great potential for the exploitation of pharmaceutically active compounds.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 43\",\"pages\":\"Pages 8591-8595\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-10-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024008735\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024008735","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Visible light-promoted C3–H alkoxycarbonylation of quinoxalin-2(1H)-ones or coumarins with alkyloxalyl chlorides†
Herein, we describe a green and efficient photoredox catalytic C3–H alkoxycarbonylation between quinoxalin-2(1H)-ones or coumarins and readily available alkyloxalyl chlorides under ambient conditions. A series of quinoxaline-3-carbonyl and coumarin-3-carbonyl compounds are prepared through the radical addition of in situ-generated alkoxycarbonyl radicals. Notably, this protocol features mild conditions, operational simplicity, and excellent functional group tolerance. More importantly, the carboxylated products can be readily derivatized into other important compounds that would be of great potential for the exploitation of pharmaceutically active compounds.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.