NHC Ligand Effects on Ru-Catalyzed Cross-Metathesis of Renewable Materials

As petrochemical resources become increasingly scarce and expensive, much attention has been focused on renewable resources from biomass as alternative options for producing basic building blocks for chemical manufacturing. Catalytic olefin metathesis represents a powerful tool to transform biosourc...

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Bibliographic Details
Main Authors: Veronica Paradiso, Raffaele Contino, Fabia Grisi
Format: Article
Language:English
Published: MDPI AG 2020-08-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/10/8/904
Description
Summary:As petrochemical resources become increasingly scarce and expensive, much attention has been focused on renewable resources from biomass as alternative options for producing basic building blocks for chemical manufacturing. Catalytic olefin metathesis represents a powerful tool to transform biosourced structural motifs in valuable commodity, fine, and specialty chemicals. In that respect, the appropriate choice of the catalyst is the key issue of each metathesis transformation. The current study examines the influence of different <i>N</i>-heterocyclic carbene (NHC) ligands containing one or two <i>N</i>-alkyl substituents on the efficiency of Hoveyda–Grubbs-type catalysts in the cross-metathesis reaction of ethyl oleate with <i>cis</i>-1,4-diacetoxy-2-butene and cross-metathesis of eugenol acetate with <i>cis</i>-1,4-dichloro-2-butene. Interestingly, the introduction of alkyl <i>N</i>-substituents in the NHC ligand was revealed as beneficial for catalytic performances in the examined cross-metathesis (CM) reactions, leading to higher activity and/or selectivity than those observed in the presence of the classical, commercially available Hoveyda–Grubbs second generation catalyst (<b>HGII</b>).
ISSN:2073-4344