Abstract
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 N-heterocyclic carbene (NHC) ligands containing one or two N-alkyl substituents on the efficiency of Hoveyda–Grubbs-type catalysts in the cross-metathesis reaction of ethyl oleate with cis-1,4-diacetoxy-2-butene and cross-metathesis of eugenol acetate with cis-1,4-dichloro-2-butene. Interestingly, the introduction of alkyl N-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 (HGII).
Highlights
Olefin metathesis is a highly versatile method for the construction of new carbon–carbon double bonds, which finds important applications in the synthesis of pharmaceuticals, petrochemicals, polymers, and specialty chemicals [1,2,3].In recent years, the gradual depletion of fossil resources and the strong need to limit the adverse environmental and health impacts of petroleum-based chemicals have pushed towards the use of renewable natural resources as green alternatives [4]
In the olefin metathesis field, readily available and inexpensive plant-derived molecules containing carbon–carbon double bonds are currently considered ideal raw materials to be employed for the synthesis of valuable compounds for the chemical industry [5,6,7,8,9,10,11]
The CM of unsaturated fatty acid esters with various functional groups offers a versatile route for the synthesis of α,ω-difunctional compounds, which serve as chemical intermediates and polymer precursors
Summary
Olefin metathesis is a highly versatile method for the construction of new carbon–carbon double bonds, which finds important applications in the synthesis of pharmaceuticals, petrochemicals, polymers, and specialty chemicals [1,2,3].In recent years, the gradual depletion of fossil resources and the strong need to limit the adverse environmental and health impacts of petroleum-based chemicals have pushed towards the use of renewable natural resources as green alternatives [4]. Among all renewable raw materials, unsaturated fatty acid esters from vegetable oils, such as methyl or ethyl oleate, emerge as the most attractive chemical platforms for olefin metathesis. These compounds, can be transformed in a variety of high-value products via cross-metathesis (CM) with both unfunctionalized and functionalized olefins [12,13,14,15,16,17,18,19,20,21,22,23].
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