Organic Letters 2011-05-06

A practical and convenient fluorination of 1,3-dicarbonyl compounds using aqueous HF in the presence of iodosylbenzene.

Tsugio Kitamura, Satoshi Kuriki, Mohammad Hasan Morshed, Yuji Hori

Index: Org. Lett. 13 , 2392-2394, (2011)

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Abstract

A simple, practical, and convenient fluorination of 1,3-dicarbonyl compounds was achieved by direct use of aqueous hydrofluoric acid and iodosylbenzene (PhIO). The reaction of ethyl benzoylacetate with the reagent system of aqueous HF and PhIO in CH(2)Cl(2) gave ethyl 2-fluoro-2-benzolyacetate in 98% yield. Other 1,3-dicarbonyl compounds including β-keto esters and 1,3-diketones underwent the fluorination reaction to give the corresponding fluorinated products in good yields.