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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/7434

Title: Palladium complexes of amido-functionalized N-heterocyclic carbenes as effective precatalysts for the Suzuki-Miyaura C-C cross-coupling reactions of aryl bromides and iodides
Authors: KUMAR, S
SHAIKH, MM
GHOSH, P
Keywords: mixed aqueous-medium
heterogeneous catalysis
vibrational-spectra
transition-metal
basis-sets
ab-initio
density
air
peppsi
ligand
Issue Date: 2009
Publisher: ELSEVIER SCIENCE SA
Citation: JOURNAL OF ORGANOMETALLIC CHEMISTRY, 694(26), 4162-4169
Abstract: A series of air-stable, robust and highly active palladium based precatalysts of amido-functionalized N-heterocyclic carbenes for the Suzuki-Miyaura C-C cross-coupling reaction has been designed. In particular, the [1-R-3-{N-(benzylacetamido)imidazol-2-ylidene](2)PdCl(2) [R = i-Pr (1c) and CH(2)Ph (2c)] complexes efficiently carried out the Suzuki-Miyaura coupling of the aryl bromide and iodide substrates with phenyl boronic acid in good to excellent yields in air at 90 degrees C in 12 h. Quite interestingly, of these palladium precatalysts, the i-propyl derivative (1c) exhibited superior activity as compared to the benzyl derivative (2c). The density functional theory (DFT) studies carried out on the 1c and 2c complexes revealed the strong sigma-donating nature of the NHC ligand as reflected in their high d/b ratio [i.e. forward sigma-donation (d) to backward pi-donation (b)] of these complexes and, thus, point towards greater stability of the Pd-NHC interaction in these complexes. (C) 2009
URI: http://dx.doi.org/10.1016/j.jorganchem.2009.09.011
http://dspace.library.iitb.ac.in/xmlui/handle/10054/7434
http://hdl.handle.net/10054/7434
ISSN: 0022-328X
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