Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids

Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids

The novel dicationic metathesis catalyst [(RuCl2(H2ITapMe2)(=CH–2-(2-PrO)-C6H4))2+ (OTf−)2] (Ru-2, H2ITapMe2 = 1,3-bis(2’,6’-dimethyl-4’-trimethylammoniumphenyl)-4,5-dihydroimidazol-2-ylidene, OTf− = CF3SO3−) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was...

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Main Authors: Maximilian Koy, Hagen J. Altmann, Benjamin Autenrieth, Wolfgang Frey, Michael R. Buchmeiser
Format: Article
Language:English
Published: Beilstein-Institut 2015-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
biphasic catalysis
ionic initiators
recycling
ROMP
ruthenium
Online Access:https://doi.org/10.3762/bjoc.11.178
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spelling doaj-d75680c2df6f41d4bd5c1114634343772021-02-02T01:03:04ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-09-011111632163810.3762/bjoc.11.1781860-5397-11-178Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquidsMaximilian Koy0Hagen J. Altmann1Benjamin Autenrieth2Wolfgang Frey3Michael R. Buchmeiser4Lehrstuhl für Makromolekulare Stoffe und Faserchemie, Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49 (0)711-685-64050Lehrstuhl für Makromolekulare Stoffe und Faserchemie, Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49 (0)711-685-64050Lehrstuhl für Makromolekulare Stoffe und Faserchemie, Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49 (0)711-685-64050Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, GermanyLehrstuhl für Makromolekulare Stoffe und Faserchemie, Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany, Fax: +49 (0)711-685-64050The novel dicationic metathesis catalyst [(RuCl2(H2ITapMe2)(=CH–2-(2-PrO)-C6H4))2+ (OTf−)2] (Ru-2, H2ITapMe2 = 1,3-bis(2’,6’-dimethyl-4’-trimethylammoniumphenyl)-4,5-dihydroimidazol-2-ylidene, OTf− = CF3SO3−) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was tested in ring opening metathesis polymerization (ROMP) under biphasic conditions using a nonpolar organic solvent (toluene) and the ionic liquid (IL) 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BDMIM+][BF4−]. The structure of Ru-2 was confirmed by single crystal X-ray analysis.https://doi.org/10.3762/bjoc.11.178biphasic catalysisionic initiatorsrecyclingROMPruthenium
collection DOAJ
language English
format Article
sources DOAJ
author Maximilian Koy
Hagen J. Altmann
Benjamin Autenrieth
Wolfgang Frey
Michael R. Buchmeiser
spellingShingle Maximilian Koy
Hagen J. Altmann
Benjamin Autenrieth
Wolfgang Frey
Michael R. Buchmeiser
Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
Beilstein Journal of Organic Chemistry
biphasic catalysis
ionic initiators
recycling
ROMP
ruthenium
author_facet Maximilian Koy
Hagen J. Altmann
Benjamin Autenrieth
Wolfgang Frey
Michael R. Buchmeiser
author_sort Maximilian Koy
title Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
title_short Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
title_full Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
title_fullStr Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
title_full_unstemmed Grubbs–Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
title_sort grubbs–hoveyda type catalysts bearing a dicationic n-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2015-09-01
description The novel dicationic metathesis catalyst [(RuCl2(H2ITapMe2)(=CH–2-(2-PrO)-C6H4))2+ (OTf−)2] (Ru-2, H2ITapMe2 = 1,3-bis(2’,6’-dimethyl-4’-trimethylammoniumphenyl)-4,5-dihydroimidazol-2-ylidene, OTf− = CF3SO3−) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was tested in ring opening metathesis polymerization (ROMP) under biphasic conditions using a nonpolar organic solvent (toluene) and the ionic liquid (IL) 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BDMIM+][BF4−]. The structure of Ru-2 was confirmed by single crystal X-ray analysis.
topic biphasic catalysis
ionic initiators
recycling
ROMP
ruthenium
url https://doi.org/10.3762/bjoc.11.178
work_keys_str_mv AT maximiliankoy grubbshoveydatypecatalystsbearingadicationicnheterocycliccarbeneforbiphasicolefinmetathesisreactionsinionicliquids
AT hagenjaltmann grubbshoveydatypecatalystsbearingadicationicnheterocycliccarbeneforbiphasicolefinmetathesisreactionsinionicliquids
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AT wolfgangfrey grubbshoveydatypecatalystsbearingadicationicnheterocycliccarbeneforbiphasicolefinmetathesisreactionsinionicliquids
AT michaelrbuchmeiser grubbshoveydatypecatalystsbearingadicationicnheterocycliccarbeneforbiphasicolefinmetathesisreactionsinionicliquids
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