Electrochemical C–O bond cleavage of diaryl ethers: upcycling of lignin 4-O-5 models and polyphenylene oxide

Abstract

Selective and efficient cleavage of diaryl ether C–O bonds is significant and challenging for biomass conversion and organic synthesis. Herein, a mild and effective electrochemical method for nucleophilic aromatic substitution (SNAr) of diaryl ethers with various N- and O-nucleophiles is reported. Without the necessity of extra redox reagents and strong bases, this electrochemical SNAr reaction provides a selective and sustainable method for aromatic C–O bond cleavage and functionalization. Preliminary mechanistic studies support an electrooxidative dearomatization of diaryl ether pathway, wherein generation of a quinone imine cation facilitates the subsequent polar nucleophilic aromatic substitution through transient polarity inversion. Specifically, a practical application of this protocol is the efficient upcycling and valorization of lignin 4-O-5 models and polyphenylene oxide into value-added chemicals under ambient electrochemical conditions.

Graphical abstract: Electrochemical C–O bond cleavage of diaryl ethers: upcycling of lignin 4-O-5 models and polyphenylene oxide

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2025
Accepted
27 Jun 2025
First published
01 Jul 2025

Green Chem., 2025, Advance Article

Electrochemical C–O bond cleavage of diaryl ethers: upcycling of lignin 4-O-5 models and polyphenylene oxide

F. He, Y. Wang, X. Huang, S. Qu and J. Liu, Green Chem., 2025, Advance Article , DOI: 10.1039/D5GC02174J

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