Pd-Catalyzed Synthesis of Functionalized Arylketones from Boronic Acids and Carboxylic Acids Activated in situ with Dimethyl Dicarbonate

Lukas J. Gooßen; Lars Winkel; Arno Döhring; Keya Ghosh; Jens Paetzold

doi:10.1055/s-2002-32961

LETTER

Pd-Catalyzed Synthesis of Functionalized Arylketones from Boronic Acids and Carboxylic Acids Activated in situ with Dimethyl Dicarbonate

Lukas J. Gooßen*, Lars Winkel, Arno Döhring, Keya Ghosh, Jens Paetzold
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

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.

Key words

dimethyl dicarbonate - palladium - ketones - boronic acids - carboxylic acids - catalysis

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