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Issue 44, 2009
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Palladium-catalyzed aryl halide carbonylation–intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A

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Abstract

Exposure of a series of α-(o-haloaryl)-substituted ketones to palladium-catalyzed carbonylation conditions leads to the formation of the corresponding isocoumarins. Balloon pressure of CO is sufficient to achieve high yielding reactions, and both cyclic and acyclic ketones are efficient substrates. The utility of the method is illustrated by a short synthesis of the natural product thunberginol A.

Graphical abstract: Palladium-catalyzed aryl halide carbonylation–intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A

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Publication details

The article was received on 01 Sep 2009, accepted on 05 Oct 2009 and first published on 19 Oct 2009


Article type: Communication
DOI: 10.1039/B917839B
Citation: Chem. Commun., 2009,0, 6744-6746
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    Palladium-catalyzed aryl halide carbonylation–intramolecular O-enolate acylation: efficient isocoumarin synthesis, including the synthesis of thunberginol A

    A. C. Tadd, M. R. Fielding and M. C. Willis, Chem. Commun., 2009, 0, 6744
    DOI: 10.1039/B917839B

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