Paired Electro-synthesis of Aryl Nitriles

doi:10.6023/cjoc201903052

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2499-2506.DOI: 10.6023/cjoc201903052 Previous Articles Next Articles

ARTICLE

芳腈化合物的成对电化学合成

曹志成, 刘建超, 褚有群, 赵峰鸣, 朱英红, 佘远斌

浙江工业大学化学工程学院杭州 310032

收稿日期:2019-03-24 修回日期:2019-04-30 发布日期:2019-05-15
通讯作者: 朱英红, 佘远斌 E-mail:yhzhuchem@zjut.edu.cn;sheyb@zjut.edu.cn
基金资助:
国家重点研发计划（No.2017YFB0307503）和国家重点基础研究发展规划（973计划，No.2012CB722604）资助项目.

Paired Electro-synthesis of Aryl Nitriles

Cao Zhicheng, Liu Jianchao, Chu Youqun, Zhao Fengming, Zhu Yinghong, She Yuanbin

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032

Received:2019-03-24 Revised:2019-04-30 Published:2019-05-15
Contact: 10.6023/cjoc201903052 E-mail:yhzhuchem@zjut.edu.cn;sheyb@zjut.edu.cn
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2017YFB0307503) and the National Program on Key Basic Research Project (973 Program, No. 2012CB722604).

1. Paired Electro-synthesis of Aryl Nitriles.PDF(746KB)

Abstract

The electro-oxidation cyanation of p-methoxybenzyl alcohol (p-MeOC₆H₄CH₂OH) to prepare aryl nitriles was studied by using cyclic voltammetry (CV) and constant current electrolysis (CCE). The effects of the volume ratio of H₂O, concentration of H₂SO₄, temperature, electrode materials, current density and solvents on the electro-chemical reaction were studied. The results showed that the yield of p-methoxylbenzonitrile (p-MeOBN) was 90% in 0.15 mol·L^-1 H₂SO₄ and 30% H₂O-DMSO solution at 60℃ and 10 mA/cm² of current density when tetrabutylammonium perchlorate (Bu₄NClO₄) was used as electrolyte. The CCE of aromatic benzyl alcohols with different p-and o-substituted analogs was investigated under the optimized reaction conditions, and the yields toward formation of the corresponding aryl nitriles were 61%~92%. A plausible mechanism for the electro-oxidation cyanation procedure was proposed. A novel paired electrochemical method for the synthesis of aryl nitriles from aromatic benzyl alcohols with hydroxylamine (HAM) as "N" source and aldehyde in situ in undivided electrochemical cell was successfully developed.

Key words: aromatic benzyl alcohols, aryl nitriles, direct electro-oxidation, paired electro-synthesis

Cite this article

Cao Zhicheng, Liu Jianchao, Chu Youqun, Zhao Fengming, Zhu Yinghong, She Yuanbin. Paired Electro-synthesis of Aryl Nitriles[J]. Chin. J. Org. Chem., 2019, 39(9): 2499-2506.

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芳腈化合物的成对电化学合成

Paired Electro-synthesis of Aryl Nitriles

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