University Chemistry ›› 2024, Vol. 39 ›› Issue (12): 235-243.doi: 10.12461/PKU.DXHX202404035

Special Issue:

• Chemistry Laboratory • Previous Articles     Next Articles

Photoredox and Copper Co-Catalyzed Synthesis of α-Methyl-4-Biphenylacetonitrile

Bin Zhang1, Tiantian Li1, Yitian Song1, Ying Cheng1, Jiarong Chen1,2   

  1. 1 College of Chemistry, Central China Normal University, Wuhan 430079, China;
    2 National Demonstration Center for Experimental Chemistry Education (Central China Normal University), Wuhan 430079, China
  • Received:2024-04-07 Accepted:2024-04-23 Published:2024-12-17
  • Contact: Jiarong Chen E-mail:chenjiarong@mail.ccnu.edu.cn

Abstract: The synergistic use of photoredox and copper catalysis in free radical reactions has gained extensive application in organic synthesis due to its high yield, mild reaction conditions, excellent functional group compatibility, and environmental friendliness. In alignment with the principles of green and sustainable development, we have efficiently synthesized high-value nitrile compounds from industrial raw materials, such as olefins, commercially available trimethylcyanosilane, and water under mild conditions using visible light irradiation. This comprehensive experiment encompasses a variety of techniques, including anhydrous and anaerobic operations, thin-layer chromatography (TLC), flash column chromatography, gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) analysis. Additionally, the experiment is characterized by easily accessible starting materials, mild reaction conditions, and high reproducibility, eliminating the need for complex instrumentation. This ensures that students can enhance their experimental skills, foster their innovative capabilities, and gain exposure to the forefront of organic chemistry. Hence, this experiment holds significant practical and educational value.

Key words: Visible-light photocatalysis, Copper catalysis, Olefin conversion, Nitrile compounds, Organic chemistry experiment