University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2109108.doi: 10.3866/PKU.DXHX202109108

Special Issue:

Previous Articles     Next Articles

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

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