Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions

Abstract An electrochemical Meerwein arylation reaction was reported for the synthesis of aryl-benzoquinone derivatives. In this work, efficient electrochemical synthesis of aryl-benzoquinone derivatives by direct electrolysis of aqueous solution containing hydroquinone and aryldiazonium salts in ba...

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Main Authors: Mozhdeh Malmir, Davood Nematollahi, Ali Sadatnabi, Sajad Shanehsaz
Format: Article
Language:English
Published: Nature Portfolio 2025-05-01
Series:Scientific Reports
Subjects:
Online Access:https://doi.org/10.1038/s41598-025-02504-y
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author Mozhdeh Malmir
Davood Nematollahi
Ali Sadatnabi
Sajad Shanehsaz
author_facet Mozhdeh Malmir
Davood Nematollahi
Ali Sadatnabi
Sajad Shanehsaz
author_sort Mozhdeh Malmir
collection DOAJ
description Abstract An electrochemical Meerwein arylation reaction was reported for the synthesis of aryl-benzoquinone derivatives. In this work, efficient electrochemical synthesis of aryl-benzoquinone derivatives by direct electrolysis of aqueous solution containing hydroquinone and aryldiazonium salts in batch and a homemade continuous-flow cells is reported. In the batch system, the products were obtained in a simple undivided cell equipped with a copper anode and a stainless steel cathode. In the continuous flow system, the products were obtained simply by passing hydroquinone and the aryldiazonium salt through a tube made of copper with a stainless steel rod in the center. All equipment required in both cell types is obtained from common commercial sources. This protocol is green and cost-effective due to the use of electricity and is performed under mild and safe conditions without the use of toxic solvents and catalysts.
format Article
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institution DOAJ
issn 2045-2322
language English
publishDate 2025-05-01
publisher Nature Portfolio
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series Scientific Reports
spelling doaj-art-a627f6b21fdb4ce590decd004f46a7ef2025-08-20T03:10:18ZengNature PortfolioScientific Reports2045-23222025-05-0115111410.1038/s41598-025-02504-yElectrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditionsMozhdeh Malmir0Davood Nematollahi1Ali Sadatnabi2Sajad Shanehsaz3Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina UniversityFaculty of Chemistry and Petroleum Sciences, Bu-Ali Sina UniversityFaculty of Chemistry and Petroleum Sciences, Bu-Ali Sina UniversityFaculty of Chemistry and Petroleum Sciences, Bu-Ali Sina UniversityAbstract An electrochemical Meerwein arylation reaction was reported for the synthesis of aryl-benzoquinone derivatives. In this work, efficient electrochemical synthesis of aryl-benzoquinone derivatives by direct electrolysis of aqueous solution containing hydroquinone and aryldiazonium salts in batch and a homemade continuous-flow cells is reported. In the batch system, the products were obtained in a simple undivided cell equipped with a copper anode and a stainless steel cathode. In the continuous flow system, the products were obtained simply by passing hydroquinone and the aryldiazonium salt through a tube made of copper with a stainless steel rod in the center. All equipment required in both cell types is obtained from common commercial sources. This protocol is green and cost-effective due to the use of electricity and is performed under mild and safe conditions without the use of toxic solvents and catalysts.https://doi.org/10.1038/s41598-025-02504-yAryldiazonium saltContinuous-flow cellCopper anodeCyclic voltammetryHydroquinone
spellingShingle Mozhdeh Malmir
Davood Nematollahi
Ali Sadatnabi
Sajad Shanehsaz
Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
Scientific Reports
Aryldiazonium salt
Continuous-flow cell
Copper anode
Cyclic voltammetry
Hydroquinone
title Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
title_full Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
title_fullStr Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
title_full_unstemmed Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
title_short Electrochemically induced Meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
title_sort electrochemically induced meerwein arylation as a green strategy for the synthesis of arylbenzoquinone derivatives under batch and flow conditions
topic Aryldiazonium salt
Continuous-flow cell
Copper anode
Cyclic voltammetry
Hydroquinone
url https://doi.org/10.1038/s41598-025-02504-y
work_keys_str_mv AT mozhdehmalmir electrochemicallyinducedmeerweinarylationasagreenstrategyforthesynthesisofarylbenzoquinonederivativesunderbatchandflowconditions
AT davoodnematollahi electrochemicallyinducedmeerweinarylationasagreenstrategyforthesynthesisofarylbenzoquinonederivativesunderbatchandflowconditions
AT alisadatnabi electrochemicallyinducedmeerweinarylationasagreenstrategyforthesynthesisofarylbenzoquinonederivativesunderbatchandflowconditions
AT sajadshanehsaz electrochemicallyinducedmeerweinarylationasagreenstrategyforthesynthesisofarylbenzoquinonederivativesunderbatchandflowconditions