Wantong Yue , Qing Chen , Chuanqi Liu , Xiaoqian Wang , Zhao Du , Yilei Wang , Zhihua Peng
{"title":"偶联吡啶配体以铬催化无受体脱氢偶联可持续合成喹啉和吡咯","authors":"Wantong Yue , Qing Chen , Chuanqi Liu , Xiaoqian Wang , Zhao Du , Yilei Wang , Zhihua Peng","doi":"10.1039/d5ob00150a","DOIUrl":null,"url":null,"abstract":"<div><div>A straightforward and atom-economical method for the synthesis of quinolines and pyrroles has been reported. Using Earth-abundant, commercially available CrCl<sub>2</sub> salt as a catalyst and the inexpensive, bench-stable 6,6′-dimethyl-2,2′-dipyridyl as a ligand, this chromium-catalyzed acceptorless dehydrogenative coupling provides important heterocycles, quinolines and pyrroles, in synthetically useful yields with good functional group tolerance, releasing water and hydrogen gas as by-products. Notably, the described protocol was also found to be applicable to the sustainable synthesis of highly substituted fused polycyclic quinolines and pyrroles. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale synthesis of quinolines.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 18","pages":"Pages 4434-4440"},"PeriodicalIF":2.7000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Sustainable synthesis of quinolines and pyrroles enabled by chromium-catalyzed acceptorless dehydrogenative coupling using a bipyridine ligand†\",\"authors\":\"Wantong Yue , Qing Chen , Chuanqi Liu , Xiaoqian Wang , Zhao Du , Yilei Wang , Zhihua Peng\",\"doi\":\"10.1039/d5ob00150a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A straightforward and atom-economical method for the synthesis of quinolines and pyrroles has been reported. Using Earth-abundant, commercially available CrCl<sub>2</sub> salt as a catalyst and the inexpensive, bench-stable 6,6′-dimethyl-2,2′-dipyridyl as a ligand, this chromium-catalyzed acceptorless dehydrogenative coupling provides important heterocycles, quinolines and pyrroles, in synthetically useful yields with good functional group tolerance, releasing water and hydrogen gas as by-products. Notably, the described protocol was also found to be applicable to the sustainable synthesis of highly substituted fused polycyclic quinolines and pyrroles. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale synthesis of quinolines.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 18\",\"pages\":\"Pages 4434-4440\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-04-09\",\"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/S1477052025002812\",\"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/S1477052025002812","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Sustainable synthesis of quinolines and pyrroles enabled by chromium-catalyzed acceptorless dehydrogenative coupling using a bipyridine ligand†
A straightforward and atom-economical method for the synthesis of quinolines and pyrroles has been reported. Using Earth-abundant, commercially available CrCl2 salt as a catalyst and the inexpensive, bench-stable 6,6′-dimethyl-2,2′-dipyridyl as a ligand, this chromium-catalyzed acceptorless dehydrogenative coupling provides important heterocycles, quinolines and pyrroles, in synthetically useful yields with good functional group tolerance, releasing water and hydrogen gas as by-products. Notably, the described protocol was also found to be applicable to the sustainable synthesis of highly substituted fused polycyclic quinolines and pyrroles. Moreover, the synthetic value of this operationally simple protocol was demonstrated by gram-scale synthesis of quinolines.
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.