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Palladium-catalyzed synthesis of aryl ketones from boronic acids and carboxylic acids activated in situ by pivalic anhydride

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58582

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;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58571

Ghosh,  K.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Gooßen, L. J., & Ghosh, K. (2002). Palladium-catalyzed synthesis of aryl ketones from boronic acids and carboxylic acids activated in situ by pivalic anhydride. European Journal of Organic Chemistry, (19), 3254-3267. doi:10.1002/1099-0690(200210)2002:19<3254:AID-EJOC3254>3.0.CO;2-6.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9987-B
Abstract
A new palladium-catalyzed cross-coupling reaction between arylboronic acids and mixed anhydrides, generated in situ from carboxylic acids and pivalic anhydride, is presented. Optimization of the new catalyst and the reaction conditions led to the development of a convenient one-pot ketone synthesis directly from carboxylic and boronic acids in the presence of different (phosphane)palladium complexes in wet THF at 60 degreesC. Systematic studies were performed to elucidate the reaction mechanism of this transformation. The scope and the limitations of the new process are demonstrated by the synthesis of 33 functionalized ketones. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).