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Journal Article

Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate

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Gooßen,  L. J.
Research Group Goossen, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Group Goossen, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Group Goossen, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Paetzold,  J.
Research Group Goossen, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Group Goossen, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Winkel,  L.
Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Gooßen, L. J., Paetzold, J., & Winkel, L. (2002). Pd-catalyzed decarbonylative Heck olefination of aromatic carboxylic acids activated in situ with di-tert-butyl dicarbonate. Synlett, (10), 1721-1723. doi:10.1055/s-2002-34227.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-998F-C
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 gamma-picoline was identified to be the most effective catalyst system.