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Palladium complexes of the N-fused heterocycle derived abnormal N-heterocyclic carbenes for the much-preferred Cu-free and the amine-free Sonogashira coupling in air

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Title Palladium complexes of the N-fused heterocycle derived abnormal N-heterocyclic carbenes for the much-preferred Cu-free and the amine-free Sonogashira coupling in air
 
Creator JOHN, A
MODAK, S
MADASU, M
KATARI, M
GHOSH, P
 
Subject Palladium
Abnormal N-heterocyclic carbene (NHC)
Sonogashira reaction
Cu-free
Amine-free
DFT studies
COPPER-FREE SONOGASHIRA
RING-OPENING POLYMERIZATION
CHARGE DECOMPOSITION ANALYSIS
TRANSITION-METAL-COMPLEXES
MIXED AQUEOUS-MEDIUM
SET MODEL CHEMISTRY
RHODIUM COMPLEXES
HECK ALKYNYLATION
ARYL HALIDES
HETEROGENEOUS CATALYSIS
 
Description Abnormal N-heterocyclic carbenes of the N-fused heterocycles were employed in stabilizing a series of PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed complexes of the type (abnormal-NHC)Pdl(2)(pyridine). Specifically, imidazo[1,2-a]pyridine based abnormal complexes, trans-{(1-ethyl-2-(4-R-phenyl)-imidazol-3-ylidene[1,2-a]pyridine)}Pdl(2)(pyridine) [R= F (1b), Cl (2b), Br (3b) and Me (4b)] were synthesized from the reaction of corresponding imidazo[1,2-a]pyridinium iodide salts (1-4)a with PdCl2 in pyridine in the presence of K2CO3 as a base. The (1-4)b complexes carried out the Sonogashira couplings of the aryl bromide and iodide substrates with terminal alkynes in a mixed aqueous medium in air under the Cu-free and amine-free conditions. The density functional theory studies revealed that in the (1-4)b complexes, the C-carbene-Pd sigma-bonding interaction was significantly stronger than the trans Pd-N-pyridine sigma-bonding interaction. (C) 2013 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2014-10-16T12:27:35Z
2014-10-16T12:27:35Z
2013
 
Type Article
 
Identifier POLYHEDRON, 6420-29
http://dx.doi.org/10.1016/j.poly.2013.01.062
http://dspace.library.iitb.ac.in/jspui/handle/100/15545
 
Language en