Pd-Catalyzed Decarbonylative Heck Olefination of Aromatic Carboxylic Acids Activated in situ with Di-tert-butyl Dicarbonate

Lukas J.  Gooßen; Jens  Paetzold; Lars  Winkel

doi:10.1055/s-2002-34227

LETTER

Pd-Catalyzed Decarbonylative Heck Olefination of Aromatic Carboxylic Acids Activated in situ with Di-tert-butyl Dicarbonate

Lukas J. Gooßen*, Jens Paetzold, Lars Winkel
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062985; e-Mail: goossen@mpi-muelheim.mpg.de;

Abstract

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Abstract

The first protocol for a direct Heck olefination of aromatic carboxylic acids has been developed. By treatment with commercially available di-tert-butyl dicarbonate, the carboxylic acids are converted in situ into the mixed anhydrides, which in the presence of a palladium catalyst react with olefins to give styrene derivatives. As by-products, only volatile CO and CO₂ along with tert-butanol are formed, making the work-up of the reaction products particuarly easy. A mixture of PdCl₂, LiCl and γ-picoline was identified to be the most effective catalyst system.

Key words

carboxylic acids - catalysis - palladium - Heck reaction - di-tert-butyl dicarbonate

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