大学化学 >> 2024, Vol. 39 >> Issue (11): 225-231.doi: 10.3866/PKU.DXHX202401088

所属专题： 自由基化学

化学实验 上一篇    下一篇

银催化的开环Minisci反应——开发适合本科生的教学实验

鲁缘怡, 赵俊, 李洪爽   

  1. 山东第一医科大学(山东省医学科学院)药学院(药物研究所)先进药物递释系统全国重点实验室, 济南 250117
  • 收稿日期:2024-01-30 录用日期:2024-04-03 发布日期:2024-04-19
  • 通讯作者: 李洪爽 E-mail:hsli@sdfmu.edu.cn
  • 基金资助:
    山东第一医科大学教育教学改革研究项目(2021XY092)；山东省自然科学基金(ZR2023MB136)

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

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摘要： Minisci反应是利用亲核性的碳自由基中间体对芳杂环进行的取代反应。本研究以1-甲基环丙醇和苯并[d]噻唑为原料在银催化、水相反应条件下发生自由基烷基化，高效合成了4-(苯并[d]噻唑-2-基)-2-丁酮，具有操作步骤简单、反应条件温和及原子经济性的优势。本反应已经本科生进行验证，将有效补充自由基化学相关知识，适合开发成为教学实验。

关键词: Minisci反应, 1-甲基环丙醇, 苯并[d]噻唑, 自由基烷基化反应, 教学实验

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