Electrolyte‐Free Electrochemical C3‐Arylmethylation of Indoles with Tertiary/Secondary <i>N</i>‐Methyl Anilines using <i>N</i>‐Methyl as the Methylene Source

An electrochemical approach devoid of electrolytes, oxidants, metals, and light is established for the C3‐arylmethylation of indoles using tertiary/secondary N ‐methyl anilines, demonstrating a wide substrate scope, with N ‐methyl serving as the methylene donor. Mechanistic investigations indicate that the presumed C3‐aminomethylated indole acts as a reactive intermediate, facilitating the formation of the arylmethylated product via radical/electrophilic addition, anodic oxidation/deprotonation, fragmentation, and cathodic reduction/protonation processes.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-06-24
DOI
https://doi.org/10.1002/adsc.9601
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Electrolyte‐Free Electrochemical C3‐Arylmethylation of Indoles with Tertiary/Secondary N‐Methyl Anilines using N‐Methyl as the Methylene Source

Sifeng Li, Chengcheng Fang, Yingqian Xu, Jian Zhen Ou et al.
1 citations
Advanced Synthesis & Catalysis
Radical Photochemical Reactions
0.94
article

Electrolyte‐Free Electrochemical C3‐Arylmethylation of Indoles with Tertiary/Secondary N‐Methyl Anilines using N‐Methyl as the Methylene Source

Sifeng Li, Chengcheng Fang, Yingqian Xu, Jian Zhen Ou, Haibiao Chen, Yijun Yu, Xiaoqing Liu, Shan Liu, Jie He
article en
1 citations

Abstract

An electrochemical approach devoid of electrolytes, oxidants, metals, and light is established for the C3‐arylmethylation of indoles using tertiary/secondary N ‐methyl anilines, demonstrating a wide substrate scope, with N ‐methyl serving as the methylene donor. Mechanistic investigations indicate that the presumed C3‐aminomethylated indole acts as a reactive intermediate, facilitating the formation of the arylmethylated product via radical/electrophilic addition, anodic oxidation/deprotonation, fragmentation, and cathodic reduction/protonation processes.

Advanced Synthesis & CatalysisVol. 367(15)
University of Science and Technology Liaoning (CN), Shenzhen Polytechnic University (CN)
Openalex Percentile: Top 25%
Radical Photochemical Reactions
0.94
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Electrolyte‐Free Electrochemical C3‐Arylmethylation of Indoles with Tertiary/Secondary <i>N</i>‐Methyl Anilines using <i>N</i>‐Methyl as the Methylene Source — Sifeng Li, Chengcheng Fang, et al. · Advanced Synthesis & Catalysis (2025) | TGRS Research Map | TGRS