Molecules 2012, 17(6), 6625-6632; doi:10.3390/molecules17066625
Article

Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents

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Received: 7 May 2012; in revised form: 29 May 2012 / Accepted: 29 May 2012 / Published: 31 May 2012
(This article belongs to the Special Issue Hypervalent Compounds)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: iodonium ylide; hypervalent iodine; dibenzoylmethane; 1,3-dicarbonyl compound; fluorination; chlorination
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MDPI and ACS Style

Gondo, K.; Kitamura, T. Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents. Molecules 2012, 17, 6625-6632.

AMA Style

Gondo K, Kitamura T. Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents. Molecules. 2012; 17(6):6625-6632.

Chicago/Turabian Style

Gondo, Keisuke; Kitamura, Tsugio. 2012. "Reaction of Iodonium Ylides of 1,3-Dicarbonyl Compounds with HF Reagents." Molecules 17, no. 6: 6625-6632.

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