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