Hiwot M. Tiruye, Solon Economopoulos, Kåre B. Jørgensen
{"title":"Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)","authors":"Hiwot M. Tiruye, Solon Economopoulos, Kåre B. Jørgensen","doi":"10.3762/bjoc.20.153","DOIUrl":null,"url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\n<p>The electrochemical oxidation of polycyclic aromatic phenols (PAPs) has been developed in a microfluidic cell to synthesize polycyclic aromatic quinones (PAQs). Methanol was used as nucleophile to trap the phenoxonium cation formed in the oxidation as an acetal, that later were hydrolysed to the quinone. Formation of hydrogen gas as the cathode reaction caused challenges in the flow cell and were overcome by recycling the reaction mixture through the cell at increased flow rate several times. The specific quinones formed were guided by the position of an initial hydroxy group on the polycyclic aromatic hydrocarbon. An available <i>para</i>-position in the PAPs gave <i>p</i>-quinones, while hydroxy groups in the 2- or 3-position led to <i>o</i>-quinones. The substrates were analysed by cyclic voltammetry for estitmation of the HOMO/LUMO energies to shed more light on this transformation. The easy separation of the supporting electrolyte from the product will allow recycling and makes this a green transformation.</p>\n<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-153-graphical-abstract.png?max-width=550' border='0'/></p>\n<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 1746–1757. doi:10.3762/bjoc.20.153</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"40 1","pages":""},"PeriodicalIF":2.2000,"publicationDate":"2024-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.153","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
The electrochemical oxidation of polycyclic aromatic phenols (PAPs) has been developed in a microfluidic cell to synthesize polycyclic aromatic quinones (PAQs). Methanol was used as nucleophile to trap the phenoxonium cation formed in the oxidation as an acetal, that later were hydrolysed to the quinone. Formation of hydrogen gas as the cathode reaction caused challenges in the flow cell and were overcome by recycling the reaction mixture through the cell at increased flow rate several times. The specific quinones formed were guided by the position of an initial hydroxy group on the polycyclic aromatic hydrocarbon. An available para-position in the PAPs gave p-quinones, while hydroxy groups in the 2- or 3-position led to o-quinones. The substrates were analysed by cyclic voltammetry for estitmation of the HOMO/LUMO energies to shed more light on this transformation. The easy separation of the supporting electrolyte from the product will allow recycling and makes this a green transformation.
Beilstein J. Org. Chem.2024,20, 1746–1757. doi:10.3762/bjoc.20.153
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The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
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