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Bifunctional nickel precatalysts of amido-functionalized N-heterocyclic carbenes for base-free Michael reaction under ambient conditions

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Title Bifunctional nickel precatalysts of amido-functionalized N-heterocyclic carbenes for base-free Michael reaction under ambient conditions
 
Creator KUMAR, S
NARAYANAN, A
RAO, MN
SHAIKH, MM
GHOSH, P
 
Subject Carbene
Nickel
Bifunctional
Catalysis
Michael reaction
RING-OPENING POLYMERIZATION
MIXED AQUEOUS-MEDIUM
TRANSITION-METAL
FISCHER-TYPE
1,3-DICARBONYL COMPOUNDS
NUCLEOPHILIC-ADDITION
CATALYTIC APPLICATION
GOLD(I) COMPLEXES
L-LACTIDE
SILVER
 
Description A series of new bifunctional nickel precatalysts, [1-(R)-3-N-(benzylacetamido)imidazol-2-ylidene](2) Ni [R Me (1b), i-Pr (2b), and CH2Ph (3b)], containing a Lewis acidic metal site and a Lewis basic amido-N site in a pendent ligand sidearm, have been successfully designed for base-free Michael addition reaction. Specifically, the nickel (1-3)b complexes catalyzed the highly desired base-free Michael addition reactions of representative cyclic 5-membered beta-dicarbonyl and beta-ketoester substrates with a variety of activated olefinic compounds in air at ambient temperature in good to excellent yield. The nickel (1-3) b complexes were synthesized from the reactions of the corresponding imidazolium chloride salts, (1-3) a, with NiCl2 center dot 6H(2)O in presence of K2CO3 as a base in 55-73% yield. The density functional theory (DFT) studies performed on the nickel complexes suggested the presence of a strong Ni-NHC sigma-interaction in these complexes. (C) 2011 Elsevier B.V. All rights reserved.
 
Publisher ELSEVIER SCIENCE SA
 
Date 2014-10-16T05:35:06Z
2014-10-16T05:35:06Z
2012
 
Type Article
 
Identifier JOURNAL OF ORGANOMETALLIC CHEMISTRY, 696(26)4159-4165
http://dx.doi.org/10.1016/j.jorganchem.2011.09.007
http://dspace.library.iitb.ac.in/jspui/handle/100/15350
 
Language en