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

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

 and *
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
* Author to whom correspondence should be addressed.
Received: 7 May 2012 / Revised: 29 May 2012 / Accepted: 29 May 2012 / Published: 31 May 2012
(This article belongs to the Special Issue Hypervalent Compounds)
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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 iodonium ylide; hypervalent iodine; dibenzoylmethane; 1,3-dicarbonyl compound; fluorination; chlorination
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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

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