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

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

doi:10.1039/C4DT00142G

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

Mathieu Rouen,^a Etienne Borré,^a Laura Falivene,^b Loic Toupet,^c Mikaël Berthod,^d Luigi Cavallo,^be Hélène Olivier-Bourbigou^d and Marc Mauduit*^a

Author affiliations

* Corresponding authors

^a Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, OMC Team, 11 allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France
E-mail: marc.mauduit@ensc-rennes.fr
Fax: (+)33-223-238-108

^b Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, I-84084 Fisciano (SA), Italy

^c Institut de Physique de Rennes - Université Rennes 1, CNRS, UMR 6251 Campus de Beaulieu Bâtiment 11A, 263 av. Général Leclerc, 35042 Rennes Cedex, France

^d IFP Energies nouvelles, Rond Point de l’échangeur de Solaize, BP3, 69360 Solaize, France

^e KAUST Catalysis Center, 4700 King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia

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.

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Article information

DOI: https://doi.org/10.1039/C4DT00142G
Article type: Paper
Submitted: 15 Jan 2014
Accepted: 14 Feb 2014
First published: 17 Feb 2014

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Dalton Trans., 2014,43, 7044-7049

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

M. Rouen, E. Borré, L. Falivene, L. Toupet, M. Berthod, L. Cavallo, H. Olivier-Bourbigou and M. Mauduit, Dalton Trans., 2014, 43, 7044 DOI: 10.1039/C4DT00142G

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Dalton Transactions