- Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents.
Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents.
Molecules (Basel, Switzerland) (2012-06-26)
Keisuke Gondo, Tsugio Kitamura
PMID22728358
ABSTRACT
Reaction of dibenzoylmethane with (diacetoxyiodo)benzene in the presence of KOH in MeCN quantitatively gave the corresponding iodonium ylide, which was treated with a HF reagent to afford the corresponding 2-fluorinated dibenzoylmethane in 14-50% yields. The similar reaction of the iodonium ylides obtained from 1-phenylbutan-1,3-dione, ethyl benzoylacetate, and ethyl p-nitrobenzoylacetate with TEA·3HF gave the corresponding fluorinated products in 17-34% yields. It is suggested that the fluorinated products were formed through the C-protonation of the ylide, followed by displacement with fluoride ion. The same reaction of the iodonium ylide of dibenzoylmethane with concentrated HCl gave the corresponding chlorinated product in 45% yield.
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