Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 692, Issue 12, Pages 2554-2563Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2007.02.044
Keywords
N-heterocyclic carbene; imidazopyridinylidene; bidentate ligands; palladium complexes; Heck reaction; Suzuki-Miyaura reaction; C-C cross-coupling
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The synthesis and characterization of new bidentate N-heterocyclic carbene ligands is described. The ligands are derived from methylene (me) and ethylene (et) bridged imidazo[1,5-a]pyridine-3-ylidenes (impy) and can be synthesized readily from imidazo[1,5-a]pyridine and the respective dihaloalkanes. Palladium(II) dihalide complexes bearing these et(impy)(2) or me(impy)(2) ligands were prepared and also structurally characterized. The angle of the impy plane vs. the C-Pd-C plane is depending on the bridging unit as well as the halide ligands. In the solid state the me(impy)(2)PdBr(2) complex forms a dimer by weak intermolecular Pd-hydrogen bridges. The activity of the Pd-complexes as catalysts for the Heck and Suzuki-Miyaura reactions was tested under various conditions. The catalysts show good activity at 120 degrees C in Heck and at 85 degrees C in Suzuki-Miyaura reactions. (c) 2007 Elsevier B.V. All rights reserved.
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