Abstract
A series of novel palladium(ii) acetylacetonato complexes bearing mesoionic carbenes (MICs) have been synthesized and characterized. The synthesis of the complexes of type (MIC)Pd(acac)I (MIC = 1-mesityl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (1), 1,4-(2,4,6-methyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (2), 1,4-(2,6-diisopropyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (3); acac = acetylacetonato) via direct metalation starting from the corresponding triazolium iodides and palladium(ii) acetylacetonate is described herein. All complexes were characterized by 1H- and 13C-NMR spectroscopy and high resolution mass spectrometry. Additionally, two of the complexes were characterized by single crystal X-ray crystallography confirming a square-planar coordination geometry of the palladium(ii) center. A delocalized bonding situation was observed within the triazolylidene rings as well as for the acac ligand respectively. Complex 2 was found to be an efficient pre-catalyst for the Suzuki-Miyaura cross coupling reaction between aryl-bromides or -chlorides with phenylboronic acid.
Highlights
N-heterocyclic carbenes (NHCs) are a very attractive class of compounds
These NHC complexes showed high catalytic activity in the Buchwald–Hartwig amination and in the we report on the synthesis of a series of novel palladium(II) acetylacetonato complexes arylation of α-ketones [85,86]
Synthesis and Characterization of the Palladium(II) Complexes procedures reported in the literature
Summary
N-heterocyclic carbenes (NHCs) are a very attractive class of compounds Because of their easy accessibility and their high complex stability, these ligands have been used extensively in organometallic chemistry in the last decades [1,2,3,4,5,6]. Apart from imidazol-5-ylidenes, 1,2,3-triazol-5-ylidenes are the most noted MICs found in the literature [16,17,18,19,20,21,22].
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