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Issue 99, 2012
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Nucleophilic fluorination of β-ketoester derivatives with HBF4

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Treating readily available α-diazo-β-ketoesters with HBF4 results in nucleophilic fluorination by the usually inert and stable tetrafluoroborate anion. The resulting α-fluoro-β-ketoesters are highly versatile synthetic intermediates, for example in the preparation of fluoro-heterocycles, as illustrated by the direct formation of fluoro-pyrimidines, -pyrazoles and -coumarins in a single step.

Graphical abstract: Nucleophilic fluorination of β-ketoester derivatives with HBF4

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Publication details

The article was received on 05 Oct 2012, accepted on 05 Nov 2012 and first published on 06 Nov 2012

Article type: Communication
DOI: 10.1039/C2CC37284C
Citation: Chem. Commun., 2012,48, 12077-12079
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    Nucleophilic fluorination of β-ketoester derivatives with HBF4

    R. Pasceri, H. E. Bartrum, C. J. Hayes and C. J. Moody, Chem. Commun., 2012, 48, 12077
    DOI: 10.1039/C2CC37284C

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