Scalable and Practical Electrooxidation of Electron‐Deficient Methylarenes to Access Aromatic Aldehydes

Abstract Aromatic aldehydes are pivotal synthetic intermediates with applications in fine chemicals, pharmaceuticals, agrochemicals, and advanced materials. Although the oxidation of methylarenes represents an ideal route to aromatic aldehydes due to the availability of starting materials, existing methods face significant challenges, including reliance on hazardous oxidants, costly catalysts, poor scalability, and limited compatibility with electron‐deficient substrates. To address these limitations, we report a practical and scalable electrochemical method for the oxidation of electron‐deficient methylarenes to access aromatic aldehydes, eliminating the need for chemical oxidants or homogeneous transition‐metal catalysts. This approach operates under industrially viable conditions—high current densities (75 mA cm⁻ 2 ), minimal electrolyte loading (0.05 equiv), and operation in an undivided cell without additives—to produce aromatic acetals, which are readily hydrolyzed to the corresponding aldehydes. The use of minimal electrolyte not only reduces costs and simplifies product isolation but also significantly enhances anodic oxidation selectivity, ensuring high efficiency and practicality. This protocol exhibits a broad substrate scope, compatibility with both batch and continuous flow systems, and exceptional scalability, as demonstrated by successful kilogram‐scale synthesis.

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Publication Details

Journal
Angewandte Chemie
Published
2025-06-07
DOI
https://doi.org/10.1002/ange.202504612
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Scalable and Practical Electrooxidation of Electron‐Deficient Methylarenes to Access Aromatic Aldehydes

Hai‐Chao Xu, Chong Huang
Angewandte Chemie
Oxidative Organic Chemistry Reactions
article

Scalable and Practical Electrooxidation of Electron‐Deficient Methylarenes to Access Aromatic Aldehydes

Hai‐Chao Xu, Chong Huang
article en

Abstract

Abstract Aromatic aldehydes are pivotal synthetic intermediates with applications in fine chemicals, pharmaceuticals, agrochemicals, and advanced materials. Although the oxidation of methylarenes represents an ideal route to aromatic aldehydes due to the availability of starting materials, existing methods face significant challenges, including reliance on hazardous oxidants, costly catalysts, poor scalability, and limited compatibility with electron‐deficient substrates. To address these limitations, we report a practical and scalable electrochemical method for the oxidation of electron‐deficient methylarenes to access aromatic aldehydes, eliminating the need for chemical oxidants or homogeneous transition‐metal catalysts. This approach operates under industrially viable conditions—high current densities (75 mA cm⁻ 2 ), minimal electrolyte loading (0.05 equiv), and operation in an undivided cell without additives—to produce aromatic acetals, which are readily hydrolyzed to the corresponding aldehydes. The use of minimal electrolyte not only reduces costs and simplifies product isolation but also significantly enhances anodic oxidation selectivity, ensuring high efficiency and practicality. This protocol exhibits a broad substrate scope, compatibility with both batch and continuous flow systems, and exceptional scalability, as demonstrated by successful kilogram‐scale synthesis.

Angewandte ChemieVol. 137(33)
Xiamen University (CN)
National Natural Science Foundation of China, Ministry of Science and Technology of the People's Republic of China
Openalex Percentile: Top 90%
Oxidative Organic Chemistry Reactions
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