Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

Mathieu Rouen; Etienne Borré; Laura Falivene; Loïc J. Toupet; Mikaël Berthod; Luigi Cavallo; Hélène Olivier-Bourbigou; Marc Mauduit

doi:10.1039/c4dt00142g

Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

Mathieu Rouen, Etienne Borré, Laura Falivene, Loïc J. Toupet, Mikaël Berthod, Luigi Cavallo, Hélène Olivier-Bourbigou, Marc Mauduit

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

Air-stable Ru-indenylidene and Hoveyda-type complexes bearing new unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands combining a mesityl unit and a flexible cycloalkyl moiety as N-substituents were synthesised. Structural features, chemical stabilities and catalytic profiles in olefin metathesis of this new library of cycloalkyl-based U2-NHC Ru complexes were studied and compared with their unsymmetrical saturated NHC-Ru homologues as well as a set of commercially available Ru-catalysts bearing either symmetrical SIMes or IMes NHC ligands. © 2014 the Partner Organisations.

Original language	English (US)
Pages (from-to)	7044-7049
Number of pages	6
Journal	Dalton Transactions
Volume	43
Issue number	19
DOIs	https://doi.org/10.1039/c4dt00142g
State	Published - 2014

ASJC Scopus subject areas

Inorganic Chemistry

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10.1039/c4dt00142g

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title = "Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis",

abstract = "Air-stable Ru-indenylidene and Hoveyda-type complexes bearing new unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands combining a mesityl unit and a flexible cycloalkyl moiety as N-substituents were synthesised. Structural features, chemical stabilities and catalytic profiles in olefin metathesis of this new library of cycloalkyl-based U2-NHC Ru complexes were studied and compared with their unsymmetrical saturated NHC-Ru homologues as well as a set of commercially available Ru-catalysts bearing either symmetrical SIMes or IMes NHC ligands. {\textcopyright} 2014 the Partner Organisations.",

author = "Mathieu Rouen and Etienne Borr{\'e} and Laura Falivene and Toupet, {Lo{\"i}c J.} and Mika{\"e}l Berthod and Luigi Cavallo and H{\'e}l{\`e}ne Olivier-Bourbigou and Marc Mauduit",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financed by the European Community through the seventh framework program (CP-FP 211468-2 EUMET, grant to MR, LF and EB). MM thanks the Agence Nationale de la Recherche (grant ANR-12-CD2I-0002 CFLOW-OM), Rennes Metropole and the Region-Bretagne for their financial support concerning the development of Ru-based complexes. Dr O. Basle and C. Crevisy are gratefully acknowledged for their helpful discussion.",

year = "2014",

doi = "10.1039/c4dt00142g",

language = "English (US)",

volume = "43",

pages = "7044--7049",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "19",

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T1 - Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

AU - Rouen, Mathieu

AU - Borré, Etienne

AU - Falivene, Laura

AU - Toupet, Loïc J.

AU - Berthod, Mikaël

AU - Cavallo, Luigi

AU - Olivier-Bourbigou, Hélène

AU - Mauduit, Marc

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was financed by the European Community through the seventh framework program (CP-FP 211468-2 EUMET, grant to MR, LF and EB). MM thanks the Agence Nationale de la Recherche (grant ANR-12-CD2I-0002 CFLOW-OM), Rennes Metropole and the Region-Bretagne for their financial support concerning the development of Ru-based complexes. Dr O. Basle and C. Crevisy are gratefully acknowledged for their helpful discussion.

PY - 2014

Y1 - 2014

N2 - Air-stable Ru-indenylidene and Hoveyda-type complexes bearing new unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands combining a mesityl unit and a flexible cycloalkyl moiety as N-substituents were synthesised. Structural features, chemical stabilities and catalytic profiles in olefin metathesis of this new library of cycloalkyl-based U2-NHC Ru complexes were studied and compared with their unsymmetrical saturated NHC-Ru homologues as well as a set of commercially available Ru-catalysts bearing either symmetrical SIMes or IMes NHC ligands. © 2014 the Partner Organisations.

AB - Air-stable Ru-indenylidene and Hoveyda-type complexes bearing new unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands combining a mesityl unit and a flexible cycloalkyl moiety as N-substituents were synthesised. Structural features, chemical stabilities and catalytic profiles in olefin metathesis of this new library of cycloalkyl-based U2-NHC Ru complexes were studied and compared with their unsymmetrical saturated NHC-Ru homologues as well as a set of commercially available Ru-catalysts bearing either symmetrical SIMes or IMes NHC ligands. © 2014 the Partner Organisations.

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DO - 10.1039/c4dt00142g

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EP - 7049

JO - Dalton Transactions

JF - Dalton Transactions

IS - 19

ER -

Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

Abstract

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CCDC 876822: Experimental Crystal Structure Determination : Dichloro-(1-cyclopentyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-(isopropoxy)benzylidene)-ruthenium

CCDC 843466: Experimental Crystal Structure Determination : Dichloro-(1-cyclododecyl-3-mesitylimidazolidin-2-ylidene)-(3-phenyl-1H-inden-1-ylidene)-(tricyclohexylphosphine)-ruthenium unknown solvate

CCDC 890262: Experimental Crystal Structure Determination : (1-cyclododecyl-3-(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)-(2-{2-methyl-4-[(trifluoroacetyl)amino]phenoxy}propylidene)-dichloro-ruthenium unknown solvate

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Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 876822: Experimental Crystal Structure Determination : Dichloro-(1-cyclopentyl-3-mesityl-2,3-dihydro-1H-imidazol-2-ylidene)-(2-(isopropoxy)benzylidene)-ruthenium

CCDC 843466: Experimental Crystal Structure Determination : Dichloro-(1-cyclododecyl-3-mesitylimidazolidin-2-ylidene)-(3-phenyl-1H-inden-1-ylidene)-(tricyclohexylphosphine)-ruthenium unknown solvate

CCDC 890262: Experimental Crystal Structure Determination : (1-cyclododecyl-3-(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)-(2-{2-methyl-4-[(trifluoroacetyl)amino]phenoxy}propylidene)-dichloro-ruthenium unknown solvate

Cite this