Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 8, Pages 1950-1955Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604934
Keywords
carbenes; C-C bond formation; heterocycles; homogeneous catalysis; metathesis
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Funding
- National Science Centre (Poland) [UMO-2014/15/B/ST5/02156]
- Centre National de la Recherche Scientifique (CNRS)
- Chinese Scholarship Council
- Region Midi-Pyrenees
- CNRS
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N-Heterocyclic carbene (NHC) ligands IMes(NMe2) and IMesd(2)(2)((NMe)()) derived from the well-known IMes ligand by substituting the carbenic heterocycle with one and two dimethylamino groups, respectively, were employed for the synthesis of second-generation Grubbs-and Grubbs-Hoveyda-type ruthenium metathesis precatalysts. Whereas the stability of the complexes was found to depend on the degree of dimethylamino-substitution and on the type of complex, the backbone-substitution was shown to have a positive impact on their catalytic activity in ring-closing metathesis, with a more pronounced effect in the second-generation Grubbs-type series. The new complexes were successfully implemented in a number of challenging olefin metathesis reactions leading to the formation of tetra-substituted C=C double bonds and/or functionalized compounds.
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