{"title":"Chiral 3,3′-diaroyl BINOL phosphoric acids: syntheses and evaluation in asymmetric transfer hydrogenation, photophysical, and electrochemical studies†","authors":"Muthupandi Karthick , Nagamalla Someshwar , Chinnasamy Ramaraj Mariappan , Alagunambi Ramasubbu , Chinnasamy Ramaraj Ramanathan","doi":"10.1039/d4ob02097a","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient synthesis of enantiomerically pure 3,3′-diaroyl BINOLs is accomplished through chemoselective Weinreb ketone synthesis from the Weinreb amide derivative of chiral BINOL-3,3′-dicarboxylic acid using a Grignard reagent. This protocol facilitated the introduction of the aroyl group at the 3,3′-position of binaphthol. The 3,3′-diaroyl BINOL phosphoric acid has been prepared and evaluated for asymmetric transfer hydrogenation of 2-aryl/alkyl quinolines. The 3,3′-diaroyl BINOL phosphoric acids are found to be efficient catalysts in the hydrogenation of 2-aryl quinolines using Hantzsch ester to generate 2-aryl tetrahydroquinolines in excellent yields with moderate enantioselectivity. The presence of aroyl units, a photosensitizer core, in 3,3′-diaroyl BINOL prompted us to evaluate their photophysical and electrochemical properties, as these molecules may be a potential candidate for asymmetric photocatalysis.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 13","pages":"Pages 3112-3125"},"PeriodicalIF":2.7000,"publicationDate":"2025-02-26","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/S147705202500148X","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
An efficient synthesis of enantiomerically pure 3,3′-diaroyl BINOLs is accomplished through chemoselective Weinreb ketone synthesis from the Weinreb amide derivative of chiral BINOL-3,3′-dicarboxylic acid using a Grignard reagent. This protocol facilitated the introduction of the aroyl group at the 3,3′-position of binaphthol. The 3,3′-diaroyl BINOL phosphoric acid has been prepared and evaluated for asymmetric transfer hydrogenation of 2-aryl/alkyl quinolines. The 3,3′-diaroyl BINOL phosphoric acids are found to be efficient catalysts in the hydrogenation of 2-aryl quinolines using Hantzsch ester to generate 2-aryl tetrahydroquinolines in excellent yields with moderate enantioselectivity. The presence of aroyl units, a photosensitizer core, in 3,3′-diaroyl BINOL prompted us to evaluate their photophysical and electrochemical properties, as these molecules may be a potential candidate for asymmetric photocatalysis.
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.