University Chemistry ›› 2024, Vol. 39 ›› Issue (11): 225-231.doi: 10.3866/PKU.DXHX202401088

Special Issue:

• Chemistry Laboratory • Previous Articles     Next Articles

Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates

Yuanyi Lu, Jun Zhao, Hongshuang Li   

  1. State Key Laboratory of Advanced Drug Delivery and Release Systems, School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, China
  • Received:2024-01-30 Accepted:2024-04-03 Published:2024-04-19
  • Contact: Hongshuang Li E-mail:hsli@sdfmu.edu.cn

Abstract: The substitution of heteroaromatics by nucleophilic carbon-centered radicals is known as the Minisci reaction. In this study, efficient synthesis of 4-(benzo[d]thiazol-2-yl)butan-2-one was achieved through radical alkylation between 1-methylcyclopropan-1-ol and benzo[d]thiazole under silver-catalyzed and aqueous conditions. This method offers advantages such as simple operation procedures, mild reaction conditions, and excellent atom-economy. Undergraduates have successfully validated this reaction, making it a suitable candidate for a teaching experiment that effectively supplements knowledge in radical chemistry.

Key words: Minisci reaction, 1-Methylcyclopropan-1-ol, Benzo[d]thiazole, Radical alkylation, Teaching experiment