J. Turek, I. Panov, M. Semler
Jun 11, 2014
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Organometallics
Abstract
Six palladium(II) complexes bearing three different triazole-based N-heterocyclic carbene (NHC) ligands, [1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, 1-tert-butyl-4-(2-methoxyphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide, and 1-tert-butyl-4-(4-methylphenyl)-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide], were synthesized and fully characterized. NMR spectroscopy and X-ray diffraction analysis revealed that the amino-group-substituted NHC ligand is coordinated in bidentate fashion, forming a monocarbene chelate complex with an additional intramolecular Pd ← N bond with the nitrogen donor atom. The 4-methylphenyl- and 2-methoxyphenyl-substituted NHC ligands coordinate as C-monodentate donors, forming simple biscarbene Pd(II) complexes. The evaluation of the catalytic performance in the Suzuki–Miyaura cross-coupling reaction revealed very promising performance of the intramolecularly coordinated monocarbene complexes under relatively mild conditions even in direct comp...