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Journal Article

Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate

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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/persons59115

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;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58518

Döhring,  A.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department List, 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;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58861

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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Citation

Gooßen, L. J., Winkel, L., Döhring, A., Ghosh, K., & Paetzold, J. (2002). Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate. Synlett, (8), 1237-1240. doi:10.1055/s-2002-32961.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-99BA-C
Abstract
Highly efficient catalyst systems were developed that allow the palladium-catalyzed cross-coupling of arylboronic acids with carboxylic acids activated in situ with dimethyl dicarbonate at room temperature. As byproducts, only methanol, CO2, and boric acid are formed, making the isolation of the products particularly easy. Thus, many functionalized ketones are conveniently accessible from boronic and carboxylic acids in the presence of 1.5 equivalents of dimethyl dicarbonate and Pd(OAc)(2)-P(p-MeOPh)(3) as the catalyst, The presence of small amounts of water and a ligand-Pd ratio lower than 4 is crucial for achieving good yields at low temperatures.