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Copper-Catalyzed Three-Component Reactions of α-Ketoaldehyde, 1,3-Dicarbonyl Compound, and Organic Boronic Acid in Water: A Route to 1,4-Diketones

Qi Xia, Xiang Li, Xi Fu, Yaxuan Zhou, Yanqing Peng, Jiayi Wang* and Gonghua Song*

*School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China, Email:,

Q. Xia, X. Li, X. Fu, Y. Zhou, Y. Peng, J. Wang, G. Song, J. Org. Chem., 2021, 86, 9914-9923.

DOI: 10.1021/acs.joc.1c01100

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CuO catalyzes a three-component reaction of α-ketoaldehydes, 1,3-dicarbonyl compounds, and organic boronic acids in water to provide a wide range of products containing 1,3- and 1,4-diketones. The method offers use of readily available starting materials, wide substrate scope, excellent yields, gram-scale synthesis, and mild reaction conditions.

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proposed mechanism

Key Words

active methylenes (substitution, benzylation), arylation, 1,4-diketones, multicomponent reactions

ID: J42-Y2021