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  • Title: Pd-catalyzed arylation of silyl enol ethers of substituted alpha-fluoroketones.
    Author: Guo Y, Twamley B, Shreeve JM.
    Journal: Org Biomol Chem; 2009 Apr 21; 7(8):1716-22. PubMed ID: 19343262.
    Abstract:
    Alpha-fluoro-alpha-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either alpha-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an alpha-fluoroketone requires a strong base, such as potassium tert-butoxide, and under these conditions the presence of a base-sensitive functional group is not compatible. However, good functional tolerance was achieved when the anionic coupling moieties were generated from the silyl enol ethers obtained by reacting alpha-fluoroketones with tetrabutylammonium (tripheny1silyl)difluorosilicate (TBAT) as the fluoride source under nearly neutral conditions. The aryl halides with a carbmethoxy, nitro, cyano or carbonyl group were used. The reaction with nonfluorinated silyl enol ether 1h gave a cross-coupling product in low yield.
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