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
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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
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Creator |
KUMAR, S
SHAIKH, MM GHOSH, P |
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Subject |
mixed aqueous-medium
heterogeneous catalysis vibrational-spectra transition-metal basis-sets ab-initio density air peppsi ligand carbenes functionalized nhc suzuki-miyaura coupling organometallic catalysis palladium-nhc complex |
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Description |
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
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Publisher |
ELSEVIER SCIENCE SA
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Date |
2011-07-28T15:13:29Z
2011-12-26T12:59:49Z 2011-12-27T05:52:43Z 2011-07-28T15:13:29Z 2011-12-26T12:59:49Z 2011-12-27T05:52:43Z 2009 |
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Type |
Article
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Identifier |
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 694(26), 4162-4169
0022-328X 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 |
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Language |
en
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