Synthesis and Application of N-Heterocyclic Carbene–Palladium Ligands with Glycerol Dendrons for the Suzuki–Miyaura Cross-Coupling in Water

Maike C. Lukowiak; Markus Meise; Rainer Haag

doi:10.1055/s-0034-1378533

Synlett, Table of Contents

Synlett 2014; 25(15): 2161-2165
DOI: 10.1055/s-0034-1378533

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Synthesis and Application of N-Heterocyclic Carbene–Palladium Ligands with Glycerol Dendrons for the Suzuki–Miyaura Cross-Coupling in Water

Maike C. Lukowiak

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 Email: haag@chemie.fu-berlin.de

,

Markus Meise

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 Email: haag@chemie.fu-berlin.de

,

Rainer Haag*

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 Email: haag@chemie.fu-berlin.de

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Abstract

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Abstract

Highly active glycerol-dendron-supported N-heterocyclic carbene–palladium catalysts with catalytic sites at the core position were obtained with an efficient modular synthesis. A symmetrical ligand structure was designed to build a larger microenvironment by increasing the number of dendron generations. The catalytic activity was tested in Suzuki–Miyaura cross-coupling reactions. Deprotection of the dendritic supported catalysts allowed the catalytic reaction to take place in neat water, which is highly desirable for a more sustainable processing. A positive dendritic effect was observed for coupling of activated and nonactivated bromoaryls.

Key words

supported catalysis - dendrimers - carbene complexes - palladium - cross-coupling - green chemistry

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