Citation: Lili Jiang, Shaoyu Zheng, Xuejiao Liu, Xiaomin Xie. Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching[J]. University Chemistry, ;2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004 shu

Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching

1.
Instrumental Analysis Center, Shanghai Jiao Tong University, Shanghai 200240, China;
2.
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Xiaomin Xie, xiaominxie@sjtu.edu.cn
Received Date: 10 August 2024
Revised Date: 4 November 2024

Transition-metal-catalyzed coupling reactions are among the most important methodologies in modern organic synthesis. However, due to the cost of catalysts and specific reaction conditions, these reactions have not been widely adopted in undergraduate laboratory courses. To allow students to experience the development of modern organic chemistry and the principles of green chemistry firsthand, we designed a copper-catalyzed oxidative coupling reaction between aryl boronic acids and alkyl sulfinates to synthesize aryl sulfones. The reaction uses copper acetate (Cu(OAc)₂) and N-methylimidazole as catalysts, with air as the oxidant. The coupling of 4-acetylphenylboronic acid with sodium methylsulfonate results in the formation of 4-(methylsulfonyl)phenyl ethanone in moderate yield. This experiment involves anhydrous techniques, microscale reagent handling, thin-layer chromatography, rotary evaporation, and melting point determination. Additionally, the experiment can be extended into an exploratory exercise, enabling students to investigate the key factors influencing transition metal-catalyzed organic reactions. It fosters the development of scientific research skills and enhances students' overall experimental competence. The experiment has been successfully implemented in undergraduate laboratory courses.
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