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À propos de : Zinc-Mediated C−C Bond SigmatropicRearrangement: A New and EfficientMethodology for the Synthesis of β-Diketones        

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  • Zinc-Mediated C−C Bond SigmatropicRearrangement: A New and EfficientMethodology for the Synthesis of β-Diketones
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  • A new and efficient methodology has been developed forthe synthesis of β-diketones from aromatic α-bromo ketonesin the presence of Furukawa reagent under mild conditions.The present transformation is proposed to proceed via aReformatsky-type reaction of α-bromo ketones, followed byC−C bond sigmatropic rearrangement of the aldolate intermediate to give β-diketones in moderate to good isolatedyields, while aliphatic α-bromomethyl ketones resulted inthe formation of 2,4-disubstituted furans or cis-1,2-disubstituted cyclopropanols in moderate yields. The scope of thisprocess was investigated, and a tentative mechanism wasproposed.
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