Article (Scientific journals)
Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors in ruthenium-arene catalysts for olefin metathesis and cyclopropanation
Tudose, Adriana; Demonceau, Albert; Delaude, Lionel
2006In Journal of Organometallic Chemistry, 691 (24-25), p. 5356-5365
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Keywords :
cyclooctene; styrene; ring-opening metathesis polymerization; cyclopropanation; homogeneous catalysis
Abstract :
[en] Five imidazol(in)ium-2-carboxylates bearing cyclohexyl, mesityl, or 2,.6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding N-heterocyclic carbenes (NHCs) by reaction with carbon dioxide. They were characterized by IR and NMR spectroscopies, and by TGA. Their ability to act as NHC precursors for in situ catalytic applications was probed in ruthenium-promoted olefin metathesis and cyclopropanation reactions. When visible light induced ring-opening metathesis polymerization of cyclooctene or cyclopropanation of styrene with ethyl diazoacetate were carried out at 60 degrees C in the presence of [RuCl2(p-cymene)](2), the NHC (.) CO2 adducts and their NHC (.) HX counterparts (X = Cl, BF4) displayed similar activities. When metathesis polymerizations were performed at room temperature, the carboxylates proved far superior to the corresponding imidazol(in)ium acid salts. They displayed the same level of activity as the preformed RuCl2(p-cymene)(IMes) complex, whereas the combination of NHC (.) HX and KO-t-Bu were almost totally inactive. Results obtained for cyclopropanation reactions at room temperature did not show such a large discrepancy of behavior between the two types of adducts. (c) 2006 Elsevier B.V. All rights reserved.
Disciplines :
Chemistry
Author, co-author :
Tudose, Adriana
Demonceau, Albert ;  Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Delaude, Lionel  ;  Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Language :
English
Title :
Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors in ruthenium-arene catalysts for olefin metathesis and cyclopropanation
Publication date :
2006
Journal title :
Journal of Organometallic Chemistry
ISSN :
0022-328X
Publisher :
Elsevier Science, Lausanne, Switzerland
Volume :
691
Issue :
24-25
Pages :
5356-5365
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 26 June 2009

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