Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.jorganchem.2005.04.053
Title: Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity
Authors: Huynh, H.V. 
Ho, J.H.H.
Neo, T.C.
Koh, L.L. 
Keywords: Heck coupling reaction
Homogeneous catalysis
N-Heterocyclic carbene
Palladium
Issue Date: 15-Aug-2005
Citation: Huynh, H.V., Ho, J.H.H., Neo, T.C., Koh, L.L. (2005-08-15). Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity. Journal of Organometallic Chemistry 690 (16) : 3854-3860. ScholarBank@NUS Repository. https://doi.org/10.1016/j.jorganchem.2005.04.053
Abstract: Reaction of N,N′-dimethylbenzimidazolyl iodide (A) with Pd(OAc) 2 in DMSO gives selectively trans-bis(N,N′- dimethylbenzimidazoline-2-ylidene) palladium(II) diiodide (trans-2) in 77% yield. The selective formation of the trans-coordination isomer and thus the cis-trans rearrangement is driven by the insolubility of trans-2 in DMSO. X-ray single-crystal diffraction analysis and 13C NMR spectroscopy confirm the trans-geometry of the square planar Pd(II) complex. Catalytic studies show that cis-1 and trans-2 are highly efficient in the Mizoroki-Heck coupling reaction of aryl bromides and activated aryl chlorides both in DMF and [N(n-C4H9)4]Br as ionic liquid. The catalytic activities of Pd(II) complexes with N-heterocyclic carbene ligands derived from benzimidazole are comparable to their imidazole-derived analogues. © 2005 Elsevier B.V. All rights reserved.
Source Title: Journal of Organometallic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/94846
ISSN: 0022328X
DOI: 10.1016/j.jorganchem.2005.04.053
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