Citation: Jinyao Du, Xingchao Zang, Ningning Xu, Yongjun Liu, Weisi Guo. Electrochemical Thiocyanation of 4-Bromoethylbenzene[J]. University Chemistry, ;2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039 shu

Electrochemical Thiocyanation of 4-Bromoethylbenzene

College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong Province, China

Received Date: 10 October 2023
Revised Date: 5 January 2024

This study translates the research achievements of the National Undergraduate Innovation Training Program (research on electrochemical-promoted benzylic thiocyanation) into an innovative undergraduate organic chemistry experiment. Organic electrosynthesis has emerged as a prominent research area in organic synthesis due to its environmentally friendly, controllable, and easily scalable characteristics. However, the application of electrochemical-promoted organic reactions has not been widely incorporated into undergraduate organic chemistry experiments. This experiment successfully demonstrates the electrochemical-promoted thiocyanation of p-bromoethylbenzene at room temperature, utilizing readily available trimethylsilyl isothiocyanate. By integrating the outcomes of the “National Innovation Program” research into undergraduate organic chemistry experiments, students are guided to foster innovative thinking and embrace the concept of “green synthesis”.
- Organic electrosynthesis,
- Green synthesis,
- Thiocyanate,
- Organic chemistry experiment
1. [1]
2. [2]
  Wang, N.; Saidhareddy, P.; Jiang,X. Nat. Prod. Rep. 2020, 37, 246.
3. [3]
4. [4]
  Castanheiro, T.; Suffert, J.;Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494.
5. [5]
  Renard, P.; Schwebel, H.; Vayron,P.; Leclerc, E.; Dias, S.; Mioskowski C. Tetrahedron Lett. 2001, 42,8479.
6. [6]
  Yan, M.; Kawamata, Y.; Baran, P.S. Chem. Rev. 2017, 117, 13230.
7. [7]
  Novaes, L. F. T.; Liu, J.; Shen,Y.; Lu, L.; Meinhardt, J. M.; Lin, S. Chem. Soc. Rev.2021, 50, 7941.
8. [8]
  Hou, Z. W.; Liu, D. J.; Xiong,P.; Lai, X. L.; Song. J.; Xu, H. C. Angew. Chem. Int. Ed. 2021, 60,2943.
9. [9]
  Niu, L.; Jiang, C.; Liang, Y.;Liu, D.; Bu, F.; Shi, R.; Chen, H.; Chowdhury, A. D.; Lei, A. J. Am. Chem.Soc. 2020, 142, 17693.
10. [10]
  Liu, D.; Zhang, Z.; Yu, J.;Chen. H.; Lin. X.; Li, M.; Wen, L.; Guo, W. Org. Chem. Front. 2022,9, 2963.
11. [11]
12. [12]
  Zhang, S.; Li, Y.; Wang, T.; Li,M.; Wen. L.; Guo, W. Org. Lett. 2022, 24, 1742.
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