University Chemistry ›› 2022, Vol. 37 ›› Issue (7): 2111049.doi: 10.3866/PKU.DXHX202111049

• Chemistry Laboratory • Previous Articles     Next Articles

Study on Electrochemical Selective C-H Azolation of Phenol Derivatives

Zheng Cao, Ling Lin, Yan Wu, Shiyu Hu, Xiaojian Liao(), Pengju Feng()   

  • Received:2021-11-15 Accepted:2021-12-03 Published:2022-01-11
  • Contact: Xiaojian Liao,Pengju Feng E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn

Abstract:

Electrochemical organic synthesis uses electrons as clean reagents, and has developed rapidly in recent years. This research explores the phenol derivatives and azoles as raw materials to achieve dehydrogenation coupling through electrochemical oxidation, and the construction of C-N bonds for the synthesis of N-azolated aromatic products. Subsequently, the reproducibility of the reaction and the compatibility of substrate were studied to ultimately establish an operation process suitable for undergraduate innovative laboratory research. The experiment involves C-H functionalization reaction, which is the current frontier of organic synthesis scientific research. The reaction operation is simple, safe and efficient. Moreover, the reaction time is controllable via tuning the electricity. The reaction can be monitored by using thin-layer chromatography. The products can be separated and purified by silica gel column chromatography, and the structure can be analyzed by mass spectroscopy and nuclear magnetic resonance spectroscopy. The reaction is based on green organic synthesis to develop practical synthetic methods for nitrogen-containing compounds, by comprehensively applying cross-disciplinary knowledge of organic chemistry and physical chemistry.

Key words: Electrosynthesis, C-N coupling, C-H functionalization, Green chemistry, N-Azolation

MSC2000: 

  • G64