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Issue 18, 2018
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Stable ruthenium olefin metathesis catalysts bearing symmetrical NHC ligands with primary and secondary N-alkyl groups

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Abstract

Four novel stable Hoveyda–Grubbs-type catalysts containing N,N′-dineopentyl- and N,N′-dicyclohexyl-substituted N-heterocyclic carbene (NHC) ligands with syn and anti phenyl groups on the ring backbone were synthesized and fully characterized. The catalytic potential of these complexes was investigated in metathesis reactions of both standard and renewable substrates. Compared to the Hoveyda–Grubbs second generation catalyst (HGII), all of the new catalysts showed high performances in most of the examined metathesis transformations. In particular, N,N′-dicyclohexyl catalysts gave improved results in the challenging ring-closing metathesis (RCM) reaction to form tetrasubstituted olefins, while catalysts with neopentyl N-groups were found to be more active and Z-selective in cross-metathesis (CM) reactions. Modest enantioselectivities in the asymmetric ring-closing metathesis (ARCM) of achiral trienes with different steric hindrance were observed in the presence of catalysts bearing chiral C2-symmetric NHC ligands.

Graphical abstract: Stable ruthenium olefin metathesis catalysts bearing symmetrical NHC ligands with primary and secondary N-alkyl groups

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Publication details

The article was received on 14 Feb 2018, accepted on 11 Apr 2018 and first published on 27 Apr 2018


Article type: Paper
DOI: 10.1039/C8DT00619A
Citation: Dalton Trans., 2018,47, 6615-6627
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    Stable ruthenium olefin metathesis catalysts bearing symmetrical NHC ligands with primary and secondary N-alkyl groups

    C. Ambrosio, V. Paradiso, C. Costabile, V. Bertolasi, T. Caruso and F. Grisi, Dalton Trans., 2018, 47, 6615
    DOI: 10.1039/C8DT00619A

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