Bifunctional nickel precatalysts of amido-functionalized N-heterocyclic carbenes for base-free Michael reaction under ambient conditions
DSpace at IIT Bombay
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Title |
Bifunctional nickel precatalysts of amido-functionalized N-heterocyclic carbenes for base-free Michael reaction under ambient conditions
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Creator |
KUMAR, S
NARAYANAN, A RAO, MN SHAIKH, MM GHOSH, P |
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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 |
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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.
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Publisher |
ELSEVIER SCIENCE SA
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Date |
2014-10-16T05:35:06Z
2014-10-16T05:35:06Z 2012 |
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Type |
Article
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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 |
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Language |
en
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