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A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones

✍ Scribed by Hiroshi Hata; Takeshi Kobayashi; Hideki Amii; Kenji Uneyama; John T. Welch

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
284 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

a-Fluoro-a,b-unsaturated ketones were prepared from trifluoromethyl ketones via a sequence involving Mg metal promoted successive double defluorination. Trifluoromethyl ketones were transformed to b,b-difluoroenol silyl ethers which were then coupled with aldehydes and ketones to b-hydroxy-a,a-difluoroketones. A second Mg-promoted defluorination of the hydroxyketones followed by acid-catalyzed hydrolysis of g-hydroxy-b-fluoroenol silyl ethers provided a-fluoro-a,b-unsaturated ketones as a final product.

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