Ruthenium catalysts supported by amino-substituted N-heterocyclic carbene ligands for olefin metathesis of challenging substrates

Vincent César (1) , Yin Zhang (1) , Wioletta Kosnik (2) , Adam Zielinski (2) , Adam A. Rajkiewicz (2) , Mirko Ruamps (1, 3) , S. Bastin (1) , Noël Lugan (1) , Guy Lavigne (1) , Karol Grela (2)

1 LCC - Laboratoire de chimie de coordination
2 Faculty of Chemistry [Warsaw]
3 UT3 - Université Toulouse III - Paul Sabatier

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.

Domaines: Chimie de coordination

Vincent César, Yin Zhang, Wioletta Kosnik, Adam Zielinski, Adam A. Rajkiewicz, et al.. Ruthenium catalysts supported by amino-substituted N-heterocyclic carbene ligands for olefin metathesis of challenging substrates. Chemistry - A European Journal, 2017, 23 (8), pp.1950-1955. ⟨10.1002/chem.201604934⟩. ⟨hal-01938386⟩