Please use this identifier to cite or link to this item: https://doi.org/10.1021/om500139b
Title: Dinuclear triazole-derived Janus-type N-heterocyclic carbene complexes of palladium: Syntheses, isomerizations, and catalytic studies toward direct C5-arylation of imidazoles
Authors: Guo, S.
Huynh, H.V. 
Issue Date: 28-Apr-2014
Citation: Guo, S., Huynh, H.V. (2014-04-28). Dinuclear triazole-derived Janus-type N-heterocyclic carbene complexes of palladium: Syntheses, isomerizations, and catalytic studies toward direct C5-arylation of imidazoles. Organometallics 33 (8) : 2004-2011. ScholarBank@NUS Repository. https://doi.org/10.1021/om500139b
Abstract: The dipalladium triazolidine-diylidene complex all-trans-[PdBr 2(CH3CN)]2(μ-ditz) (1) (ditz = 1,2,4-trimethyltriazolidine-3,5-diylidene) was synthesized via in situ deprotonation of the precursor salt with a basic metal precursor. Ligand replacements of all-trans-1 with monodentate or chelating phosphines afforded the dicarbene-bridged complexes all-cis-[PdBr2(PPh3)] 2(μ-ditz) (2) and [PdBr(DPPP)]2(μ-ditz)Br 2 (3), respectively. Bromido substitution of all-cis-2 gave tetra-acetato complex all-cis-[Pd(CH3COO)2(PPh 3)]2(μ-ditz) (4) with retention of the configuration as the predominant product. In addition, monopalladium triazolin-5-ylidene complexes trans-[PdBr2(CH3CN)(tazy)] (6, tazy =1,4-dimethyltriazolin-5-ylidene), cis-[PdBr2(PPh3)(tazy)] (7), [PdBr(DPPP)(tazy)]Br (8), and cis-[Pd(CH3COO) 2(PPh3)(tazy)] (9) were also synthesized as the respective mononuclear equivalents for comparison. A comparative catalytic study revealed the general superiority of dinuclear complexes 1-4 over their respective mononuclear counterparts 6-9 in the direct C5-arylation reaction of 1-methylimidazoles. Overall, mixed dicarbene/diphosphine complex 3 showed the best catalytic performance. © 2014 American Chemical Society.
Source Title: Organometallics
URI: http://scholarbank.nus.edu.sg/handle/10635/93596
ISSN: 15206041
DOI: 10.1021/om500139b
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