大学化学 >> 2025, Vol. 40 >> Issue (2): 332-340.doi: 10.12461/PKU.DXHX202405126

化学实验 上一篇    下一篇

“在水上”无催化剂Mukaiyama-aldol反应合成3-二氟烷基-3-羟基氧化吲哚

张梦瑶, 苟星烨, 黄友, 刘慧娟, 余金生   

  1. 华东师范大学化学与分子工程学院, 上海 200062
  • 收稿日期:2024-05-20 录用日期:2024-09-05 发布日期:2025-02-22
  • 通讯作者: 余金生 E-mail:jsyu@chem.ecnu.edu.cn
  • 基金资助:
    国家自然科学基金(22171087)

“On Water” Catalyst-Free Mukaiyama-Aldol Reaction towards 3-Difluoroalkyl 3-Hydroxyloxindole

Mengyao Zhang, Xingye Gou, You Huang, Huijuan Liu, Jinsheng Yu   

  1. School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
  • Received:2024-05-20 Accepted:2024-09-05 Published:2025-02-22
  • Contact: Jinsheng Yu E-mail:jsyu@chem.ecnu.edu.cn

摘要: 采用“任务驱动型”小组合作探究的教学模式,将前沿科研热点——“在水上”无催化剂反应策略引入有机化学实验教学。以环境友好的水为溶剂,实现了无催化剂条件下1-甲基靛红与二氟烯醇硅醚的Mukaiyama-aldol反应,高效构建了一类高附加值3-二氟烷基-3-羟基氧化吲哚。通过小组合作探究四组对照实验,比较该反应在三种常用有机溶剂(二氯甲烷、甲苯、甲醇)与水中的实验结果,引导学生自主验证以水为溶剂的“在水上”反应的优越性,使学生理解水也可以是有机反应的有效溶剂这一绿色化学的前沿研究知识点,从而打破学生对有机反应使用有机溶剂的固有认知。教学过程避免了“灌输式”教学,将学生的理性认知与直观感受有效结合,有效加深了学生对有机化学学科前沿知识的理解与掌握,是基础理论知识、科学探究、化学专业素养三者相互融合的成功尝试,有助于培养化学专业高质量人才。

关键词: 任务驱动, 小组合作, 3-二氟烷基-3-羟基氧化吲哚, “在水上”反应

Abstract: This study presents an innovative teaching approach that integrates cutting-edge research into the organic chemistry curriculum through a “task-driven” group-based inquiry model. The focus is on the environmentally friendly “on water” strategy, demonstrating a catalyst-free Mukaiyama-aldol reaction between 1-methylisatin and difluoroenoxysilane, utilizing water as the solvent. This approach efficiently constructs 3-difluoroalkyl-3-hydroxyoxindole, a high-value compound. Four comparative control experiments were conducted by student groups, using common organic solvents (dichloromethane, toluene, methanol) alongside water. The results helped students independently assess the advantages of water as a solvent in organic reactions, challenging the traditional reliance on organic solvents. This pedagogical method avoids passive, lecture-based teaching, combining theoretical understanding with hands-on experimentation to deepen students’ comprehension of green chemistry and frontier research in organic chemistry. The integration of foundational knowledge, scientific inquiry, and professional chemical skills represents a successful strategy for fostering high-quality talent in chemistry.

Key words: Task driven, Group cooperation, 3-Difluoroalkyl-3-hydroxyloxindole, “On water” reaction