大学化学 >> 2022, Vol. 37 >> Issue (5): 2109108.doi: 10.3866/PKU.DXHX202109108

所属专题: 第2届全国大学生化学实验创新设计竞赛

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电化学氧化脱氢交叉偶联构建C—N键——电化学技术在有机化学实验教学中的设计与探索

赵梦龙, 苑岱雷, 叶梓, 房芳, 于月娜()   

  • 收稿日期:2021-09-29 录用日期:2021-11-04 发布日期:2022-03-10
  • 通讯作者: 于月娜 E-mail:yuyn@sustech.edu.cn
  • 作者简介:于月娜,Email: yuyn@sustech.edu.cn
    第一联系人:

    共同第一作者,对本工作有同等贡献

  • 基金资助:
    南方科技大学校级质量工程项目(XJZLGC202116)

Electrooxidative Cross-Coupling with Hydrogen Evolution to Construct C—N Bonds: Design and Exploration of Electrochemical Technology in Organic Chemistry Laboratory Teaching

Menglong Zhao, Dailei Yuan, Zi Ye, Fang Fang, Yuena Yu()   

  • Received:2021-09-29 Accepted:2021-11-04 Published:2022-03-10
  • Contact: Yuena Yu E-mail:yuyn@sustech.edu.cn

摘要:

将绿色电化学合成策略引入教学,通过电化学氧化偶联构建C—N键,实现了芳胺对位高选择性胺化,并通过循环伏安法对反应机理进行探索。此方案为科研转化的、开放性综合有机化学实验。反应以直流恒流电为电源,在室温空气条件下进行,首先以吩噻嗪和N, N-二甲基苯胺为模板底物,对电流、电量和电解质三个影响因素进行考察;确定最优条件后接着考察芳胺的适用性;最后通过循环伏安法对反应规律进行探索。实验深入融合贯穿了前沿科研成果的科学思路与创新理念,通过实验的开展,可以提升学生专业综合素质、激发学生创新意识。

关键词: 有机电化学合成, 氧化交叉偶联, C—N键, 核磁内标法定量, 循环伏安法

Abstract:

This work provides an open comprehensive experiment, which introduces green electrochemical technology into laboratory teaching. Through electrooxidative cross-coupling, highly para-selective amination of aromatic amines was achieved, and the reaction mechanism was explored using cyclic voltammetry. The oxidative C—N amination reaction was conducted at room temperature under constant current and worked well in the presence of air. Firstly, current, quantity of electric charge, and electrolytes were measured with phenothiazine and N, N-dimethylaniline as template substrates. After determining the optimal conditions, the scope of aromatic amines was studied, and the reaction mechanism was explored using cyclic voltammetry. Experiments adapted from scientific research, such as this, can stimulate both innovative thinking and innovation consciousness in undergraduate students.

Key words: Organic electrochemical synthesis, Oxidative cross-coupling, C—N bond, Quantitative NMR, Cyclic voltammetry

MSC2000: 

  • G64