大学化学 >> 2024, Vol. 39 >> Issue (5): 388-395.doi: 10.3866/PKU.DXHX202312016

所属专题： 第4届全国大学生化学实验创新设计大赛

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氮杂环卡宾催化醛与亚硝基化合物的酰胺合成

李驰, 万继超, 龙淇羽, 吕辉, 熊英   

  1. 武汉大学化学与分子科学学院, 化学国家级实验教学示范中心(武汉大学), 武汉 430072
  • 收稿日期:2023-12-04 修回日期:2024-02-04 发布日期:2024-05-25
  • 通讯作者: 熊英 E-mail:yingxiong@whu.edu.cn
  • 基金资助:
    武汉大学化学一流本科专业建设项目

N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds

Chi Li, Jichao Wan, Qiyu Long, Hui Lv, Ying Xiong   

  1. National Demonstration Center for Experimental Chemistry Education (Wuhan University), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China
  • Received:2023-12-04 Revised:2024-02-04 Published:2024-05-25
  • Contact: Ying Xiong E-mail:yingxiong@whu.edu.cn

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摘要： 酰胺合成是有机化学重要的研究方向之一。将国际前沿的酰胺合成方法引入到基础有机化学实验教学中可以丰富教学内容并促进本科教学与科研成果之间的融合。本文报道了一个以氮杂环卡宾催化醛的极性反转为知识重点的酰胺合成实验，以苯甲醛、亚硝基苯为原料，在无水无氧条件下实现了N-羟基-N-苯基苯甲酰胺的高效合成。该实验利用薄层色谱对反应过程进行监测，并通过红外、核磁共振波谱确定了产物结构。该实验具有操作简单、反应条件温和、高原子经济性、可重复性好等特点，非常适用于本科生实验教学。本实验将极性反转这一重要概念与氮杂环卡宾催化这一科学前沿有机结合起来，有利于激发和培养学生的科研兴趣。

关键词: 酰胺, 氮杂环卡宾, 醛, 极性反转, 绿色合成

Abstract: Amidation synthesis stands as a significant area in organic chemistry. Incorporating cutting-edge amidation methods into basic organic chemistry laboratory teaching can enhance educational content and foster integration between undergraduate teaching and research achievements. Herein, we report an experiment focusing on the umpolung of aldehydes catalyzed by N-heterocyclic carbene (NHC) for amide synthesis. Utilizing benzaldehyde and nitrosobenzene as substrates, N-hydroxy-N-phenylbenzoylamide was efficiently synthesized under anhydrous and oxygen-free conditions. The reaction progress was monitored via thin-layer chromatography (TLC), and the product structure was confirmed by infrared and nuclear magnetic resonance spectroscopy. This experiment offers simplicity in operation, mild reaction conditions, high atom economy, and excellent repeatability, rendering it highly suitable for undergraduate laboratory teaching. By amalgamating the pivotal concept of umpolung with the cutting-edge science of N-heterocyclic carbene catalysis, this experiment aims to stimulate and nurture students’ interest in scientific inquiry.

Key words: Amide, N-heterocyclic carbene, Aldehyde, Umpolung, Green synthesis