Abstract: Direct functionalization of inert C―H bonds is one of the cutting-edge challenges in synthetic chemistry and is considered the “holy grail” of organic synthesis. In recent years, photohydrogen atom transfer (HAT) has developed into one of the important tools for activating inert C―H bonds. We use bulk chemical ethylene glycol and commercially available bromobenzene as starting materials and achieved an efficient synthesis 1-phenylethane-1,2-diol via photo-HAT/nickel dual catalysis. This comprehensive experiment covers a variety of techniques, including anhydrous and anaerobic procedures, thin-layer chromatography (TLC), flash column chromatography, gas chromatography-mass spectrometry (GC-MS), nuclear magnetic resonance (NMR) analysis, and other experimental operations. The experiment conditions are mild, the raw materials are cheap and readily available, the operation is simple, and no complicated equipment is required. In addition, it can not only enable students to understand the cutting-edge progress of organic chemistry, stimulate students’ interest and enthusiasm in learning chemistry, and improve students’ enthusiasm and initiative, but also enable students to fully exercise their experimental skills, cultivate students’ scientific literacy and spirit of exploring the unknown, and holds significant practical and teaching value.

Key words: Photohydrogen atom transfer, Nickel catalysis, Radical chemistry, 1-Phenylethane-1,2-diol, Organic chemistry experiment