Issue 44, 2009

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

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

Supplementary files

Article information

Article type
Communication
Submitted
01 Sep 2009
Accepted
05 Okt 2009
First published
19 Okt 2009

Chem. Commun., 2009, 6744-6746

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, 6744 DOI: 10.1039/B917839B

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