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J Org Chem. 2000 Apr 7;65(7):2204-7.

Ruthenium carbene complexes with N,N'-bis(mesityl)imidazol-2-ylidene ligands: RCM catalysts of extended scope

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  • 1Max-Planck-Institut fur Kohlenforschung, Mulheim/Ruhr, Germany.


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 alpha,beta-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.

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