Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors for the synthesis of second generation ruthenium metathesis catalysts

Sauvage, Xavier; Demonceau, Albert; Delaude, Lionel

doi:10.1002/adsc.200900422

Article (Scientific journals)

Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors for the synthesis of second generation ruthenium metathesis catalysts

Sauvage, Xavier; Demonceau, Albert; Delaude, Lionel

2009 • In Advanced Synthesis and Catalysis, 351 (11-12), p. 2031-2038

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https://hdl.handle.net/2268/20192

DOI
10.1002/adsc.200900422

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Keywords :

alkene metathesis; homogeneous catalysis; N-heterocyclic carbenes; phosphane ligands; ruthenium; zwitterions

Abstract :

[en] Five well-known ruthenium-N-heterocyclic carbene (NHC) catalysts for olefin metathesis and related reactions, including the second generation Grubbs and Hoveyda-Grubbs catalysts, were prepared by phosphane exchange between first generation ruthenium-benzylidene or indenylidene complexes and NHCs generated in situ upon thermolysis of imidazol(in)ium-2-carboxylates. Because N-heterocyclic carbene -carbon dioxide adducts (NHC · CO2) are stable zwitterionic compounds that can be stored and handled with no particular precautions, this procedure is particularly attractive from a practical point of view. Reaction courses were conveniently monitored by 31P NMR spectroscopy and the experimental conditions were carefully adjusted to obtain high yields of pure products within short periods of time.

Disciplines :

Chemistry

Author, co-author :

Sauvage, Xavier ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors for the synthesis of second generation ruthenium metathesis catalysts

Publication date :

2009

Journal title :

Advanced Synthesis and Catalysis

ISSN :

1615-4150

eISSN :

1615-4169

Publisher :

Wiley-V C H Verlag Gmbh, Weinheim, Germany

Volume :

351

Issue :

11-12

Pages :

2031-2038

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 27 August 2009

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