大学化学 >> 2026, Vol. 41 >> Issue (5): 101-108.doi: 10.12461/PKU.DXHX202510042

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

香芹酮β硼化：一个可用于展示反应选择性的教学实验

陈光欢, 王英华, 明锦辉, 凌剑, 邵志会, 卢崇道, 史勇   

  1. 云南大学化学科学与工程学院, 化学化工国家级实验教学示范中心(云南大学), 云南 昆明 650500
  • 收稿日期:2025-10-15 录用日期:2026-02-06 发布日期:2026-05-21
  • 通讯作者: 史勇 E-mail:yshi@ynu.edu.cn Yong Shi
  • 基金资助:
    国家自然科学基金项目(22561050)；云南大学教育教学改革项目(2024Y15)；云南大学大学生创新创业训练项目(S202510673139)

β-Borylation of carvone: an experiment to demonstrate reaction selectivities

Guanghuan Chen, Yinghua Wang, Jinhui Ming, Jian Ling, Zhihui Shao, Chongdao Lu, Yong Shi   

  1. National Demonstration Center for Experimental Chemistry and Chemical Engineering Education (Yunnan University), School of Chemical Science and Engineering, Yunnan University, Kunming 650500, Yunnan Province, China
  • Received:2025-10-15 Accepted:2026-02-06 Published:2026-05-21
  • Contact: Yong Shi E-mail:yshi@ynu.edu.cn

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摘要： 反应选择性是贯穿有机化学教学与科学研究始终的核心概念，因相关教学内容分散在不同章节，学生难以对其建立系统认知。为此，我们设计了香芹酮和联硼酸频哪醇酯在氯化亚铜和甲醇钠催化下，发生化学、区域和立体选择性硼化反应的教学实验项目。本新创实验将反应选择性问题集中具象化展示，帮助学生去除神秘感，建立对选择性概念的全面认知，同时涵盖整套基本操作训练，可赋予丰富的素质教育元素，适合本科有机化学实验教学。

关键词: 反应选择性, β硼化, 香芹酮, 催化反应

Abstract: Reaction selectivity constitutes a fundamental concept in both organic chemistry education and scientific research. As the relevant instructional content is typically scattered across different chapters, students often struggle to develop a systematic understanding of this concept. To address this pedagogical challenge, we have designed a teaching experiment demonstrating the chemo-, regio-, and stereoselective β-borylation of carvone with bis(pinacolato)diboron, catalyzed by copper(I) chloride and sodium methoxide. This innovative experiment effectively integrates and visually demonstrates various aspects of reaction selectivity, thereby demystifying the concept and fostering comprehensive student comprehension. The experiment also provides training in fundamental laboratory techniques while incorporating multiple elements suitable for quality-oriented education, making it particularly appropriate for undergraduate organic chemistry laboratory instruction.

Key words: Reaction selectivity, β-Borylation, Carvone, Catalytic reaction