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|Title:||Benzimidazolium-pyrazole-palladium(II) complexes: New and efficient catalysts for Suzuki, Heck and Sonogashira reactions||Authors:||Li, F.
X-ray structure determination
|Issue Date:||6-Oct-2008||Citation:||Li, F., Hor, T.S.A. (2008-10-06). Benzimidazolium-pyrazole-palladium(II) complexes: New and efficient catalysts for Suzuki, Heck and Sonogashira reactions. Advanced Synthesis and Catalysis 350 (14-15) : 2391-2400. ScholarBank@NUS Repository. https://doi.org/10.1002/adsc.200800356||Abstract:||Three unsymmetrical benzimidazoliumpyrazole N-N ligands 2-(1-propylbenzimidazolylmethyl)-3,5-di-R-pyrazole (R=H, Me, t-Bu) have been conveniently prepared and structurally analyzed. The solid lattice packingof the R=Me compound at 223 K reveals one-dimensional "zig-zag" water chains stabilized by organic molecular channels through N⋯H-O and O-H⋯O bonding. These hybrid ligands add to palladium(II) to give high yields of air-stable complexes that are fully characterized by NMR, ESI, and X-ray single-crystal crystallography. They are active Suzuki catalysts at room temperature towards cross-couplingof unactivated aryl bromides and 5- or 6-membered heteroaryl bromides with arylboronic acids with turnover frequencies (TOF) reachingas high as 60,000 h-1. Their catalytic efficiency is significantly better than that of the C-N carbene-imidazole analogue. These catalysts are also active in Heck and Sonogashira cross-coupling reactions of aryl bromides giving the desired products in good yields. These results suggested that these Pd(II) complexes with N-based hybrid ligands are versatile and efficient catalysts for different types of cross-couplingreactio ns under aerobic conditions. © 2008 Wiley-VCH VerlagGmbH & Co. KGaA.||Source Title:||Advanced Synthesis and Catalysis||URI:||http://scholarbank.nus.edu.sg/handle/10635/93166||ISSN:||16154150||DOI:||10.1002/adsc.200800356|
|Appears in Collections:||Staff Publications|
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