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Ruthenium Carbene Complexes with N,N‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Oliver R.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ackermann,  Lutz
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Thiel, O. R., Ackermann, L., Schanz, H.-J., & Nolan, S. P. (2000). Ruthenium Carbene Complexes with N,N‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope. The Journal of Organic Chemistry, 65(7), 2204-2207. doi:10.1021/jo9918504.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-3BFE-7
Abstract
The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting α,β-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium:  particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.