期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 7, 期 8, 页码 1716-1722出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b900311h
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资金
- DTRA (HDTRA) [1-071-0024]
- NSF [CHE0315275]
- ONR [N00014-06-1-1032]
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 (triphenylsilyl) 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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