{"title":"New axially chiral biaryl quinoline ligands specifically partnered with AgOTf enabled an enantioselective aza-Friedel-Crafts reaction.","authors":"Su-Fan Gao, Xiao Fu, Qian-Mao Zhang, Ren-Zhi Tang, Wen-Juan Wan, Li-Xin Wang","doi":"10.1039/d5ob00231a","DOIUrl":null,"url":null,"abstract":"<p><p>A new class of axially chiral biaryl pyridine ligands have been rationally designed and concisely prepared in two steps by Skraup-Doebner-Miller synthesis. Their proof-of-concept application in an enantioselective aza-Friedel-Crafts reaction between 2-methylindoles and isatin <i>N</i>-Boc ketimines has been evaluated. Specifically partnered with AgOTf, the new ligands effectively catalysed the reaction with excellent enantioselectivities (up to 96% ee) and 71-94% yields, and a series of multifunctional chiral 3-indolyl 3-amino-oxindoles were successfully obtained. Compared with other noble metals and chiral ligands, this Ag(I)-B1 partner is highly stable, cost-effective, facile and easily available. This work has successfully demonstrated the good performance of a new kind of axially biaryl quinoline ligands and is the first example of a silver-catalysed enantioselective aza-Friedel-Crafts reaction between 2-methylindoles and isatin <i>N</i>-Boc ketimines, and has thus enriched the application of silver salts in asymmetric catalysis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00231a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A new class of axially chiral biaryl pyridine ligands have been rationally designed and concisely prepared in two steps by Skraup-Doebner-Miller synthesis. Their proof-of-concept application in an enantioselective aza-Friedel-Crafts reaction between 2-methylindoles and isatin N-Boc ketimines has been evaluated. Specifically partnered with AgOTf, the new ligands effectively catalysed the reaction with excellent enantioselectivities (up to 96% ee) and 71-94% yields, and a series of multifunctional chiral 3-indolyl 3-amino-oxindoles were successfully obtained. Compared with other noble metals and chiral ligands, this Ag(I)-B1 partner is highly stable, cost-effective, facile and easily available. This work has successfully demonstrated the good performance of a new kind of axially biaryl quinoline ligands and is the first example of a silver-catalysed enantioselective aza-Friedel-Crafts reaction between 2-methylindoles and isatin N-Boc ketimines, and has thus enriched the application of silver salts in asymmetric catalysis.
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.
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