Diethylzinc-Mediated Cross-Coupling Reactions between Dibromoketones and Monobromo Carbonyl Compounds
Aika Takeshima
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588 Japan
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Taichi Kano
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588 Japan
Search for more papers by this authorAika Takeshima
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588 Japan
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Taichi Kano
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588 Japan
Search for more papers by this authorAbstract
A novel route to synthesize 1,4-dicarbonyl compounds is described. α,α-Dibromoketones generate zinc enolates through a diethylzinc-mediated halogen-metal exchange and react with α-bromocarbonyl compounds to furnish 1,4-dicarbonyl compounds via a second generation of zinc enolates. This cross-coupling reaction is enabled by the chemoselective formation of zinc enolates from α,α-dibromoketones in the presence of α-bromocarbonyl compounds. Chiral 1,4-dicarbonyl compounds can be obtained via the enantioselective bromination of aldehydes using a chiral secondary amine catalyst and a subsequent cross-coupling reaction between the resulting chiral α-bromoaldehydes and α,α-dibromoacetophenones.
Open Research
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