Citation: Shuai Chen, Anzai Shi, Guoqing Yang, Pengfei Xie, Feng Liu, Youai Qiu. Electrochemical demethoxyl-cyanation of methoxyarenes via S_NAr[J]. Chinese Chemical Letters, ;2025, 36(9): 110810. doi: 10.1016/j.cclet.2024.110810 shu

Electrochemical demethoxyl-cyanation of methoxyarenes via S_NAr

Shuai Chen ^a ,
Anzai Shi ^a ,
Guoqing Yang ^a ,
Pengfei Xie ^a ,
Feng Liu ^{b, *,} ,
Youai Qiu ^{a, *,}

a.
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Haihe Laboratory of Sustainable Chemical Transformations, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Department of Chemistry, Fudan University, Shanghai 200438, China

liufeng@fudan.edu.cn

qiuyouai@nankai.edu.cn

Received Date: 22 November 2024
Revised Date: 26 December 2024
Accepted Date: 28 December 2024
Available Online: 29 December 2024

Figures(4)

Herein, a metal-free electrochemical demethoxyl-cyanation of methoxyarenes via aromatic nucleophilic substitution (S_NAr) using TMSCN as a cheap cyanide source under mild conditions has been presented. This transformation utilizes commercially available reagents, cheap electrodes, and simple equipment. Diverse aryl nitriles were successfully obtained in a direct and efficient way with broad substrate scope, excellent functional group tolerance, and selective C−O bond cleavage. Furthermore, late-stage modification of biorelevant compounds and gram-scale synthesis highlighted the potential application of the strategy. Mechanistic investigations suggest that the arene cation radical was considered as the key intermediate for the transformation, and undergoing the followed S_NAr process.
- Electrochemistry,
- Aromatic nucleophilic substitution (S_NAr),
- Cyanation,
- Aryl nitriles,
- Organic electrosynthesis
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Electrochemical demethoxyl-cyanation of methoxyarenes via SNAr

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Electrochemical demethoxyl-cyanation of methoxyarenes via S_NAr