{"title":"Novel organocatalytic system of R-bian, R-mian and NHPI for selective oxidation of cumene","authors":"O.S. Koshcheeva , N.I. Kuznetsova , D.E. Babushkin , I.S. Fomenko , A.L. Gushchin","doi":"10.1016/j.mcat.2024.114658","DOIUrl":null,"url":null,"abstract":"<div><div>The paper describes the influence of a series of bis(arylimino)acenaphthenes (R-bian) and mono(arylimino)acenapthenones (R-mian) in the aerobic oxidation of cumene. The imines facilitate the decomposition of minor impurities of cumene hydroperoxide, thereby acting as catalysts for the oxidation of cumene. The relative reactivity of imines in the oxidation of cumene is correlated with the relative electron-withdrawing ability of the aryl functional groups of CF<sub>3</sub>-Ph>dpp, tmp. This is demonstrated by the reactivity of dpp-mian, tmp-mian and dpp-bian, tmp-bian<CF<sub>3</sub>-Ph-bian. A comparable interaction between R-bian and NHPI enhances the solubility of the radical catalyst in cumene and intensifies NHPI-catalyzed oxidation to attain 25–30 % conversion of cumene with dpp-bian and tmp-bian promoters. The reported results present a straightforward organocatalytic system based on the utilization of imines as catalysts and promoters.</div></div>","PeriodicalId":393,"journal":{"name":"Molecular Catalysis","volume":"570 ","pages":"Article 114658"},"PeriodicalIF":3.9000,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Molecular Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S246882312400840X","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
The paper describes the influence of a series of bis(arylimino)acenaphthenes (R-bian) and mono(arylimino)acenapthenones (R-mian) in the aerobic oxidation of cumene. The imines facilitate the decomposition of minor impurities of cumene hydroperoxide, thereby acting as catalysts for the oxidation of cumene. The relative reactivity of imines in the oxidation of cumene is correlated with the relative electron-withdrawing ability of the aryl functional groups of CF3-Ph>dpp, tmp. This is demonstrated by the reactivity of dpp-mian, tmp-mian and dpp-bian, tmp-bian<CF3-Ph-bian. A comparable interaction between R-bian and NHPI enhances the solubility of the radical catalyst in cumene and intensifies NHPI-catalyzed oxidation to attain 25–30 % conversion of cumene with dpp-bian and tmp-bian promoters. The reported results present a straightforward organocatalytic system based on the utilization of imines as catalysts and promoters.
期刊介绍：
Molecular Catalysis publishes full papers that are original, rigorous, and scholarly contributions examining the molecular and atomic aspects of catalytic activation and reaction mechanisms. The fields covered are:
Heterogeneous catalysis including immobilized molecular catalysts
Homogeneous catalysis including organocatalysis, organometallic catalysis and biocatalysis
Photo- and electrochemistry
Theoretical aspects of catalysis analyzed by computational methods
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