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Article Dans Une Revue Molecules Année : 2021

Laccase-Catalyzed Oxidation of Allylbenzene Derivatives: Towards a Green Equivalent of Ozonolysis

Mathilde Lecourt
Giorgiana Chietera
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Bernard Blerot
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Sylvain Antoniotti
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Résumé

Laccase-based biocatalytic reactions have been tested with and without mediators and optimized in the oxidation of allylbenzene derivatives, such as methyl eugenol taken as a model substrate. The reaction primarily consisted in the hydroxylation of the propenyl side chain, either upon isomerization of the double bond or not. Two pathways were then observed; oxidation of both allylic alcohol intermediates could either lead to the corresponding α,β-unsaturated carbonyl compound, or the corresponding benzaldehyde derivative by oxidative cleavage. Such a process constitutes a green equivalent of ozonolysis or other dangerous or waste-generating oxidation reactions. The conversion rate was sensitive to the substitution patterns of the benzenic ring and subsequent electronic effects.
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Dates et versions

hal-03418904 , version 1 (16-11-2021)

Identifiants

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Mathilde Lecourt, Giorgiana Chietera, Bernard Blerot, Sylvain Antoniotti. Laccase-Catalyzed Oxidation of Allylbenzene Derivatives: Towards a Green Equivalent of Ozonolysis. Molecules, 2021, 26 (19), pp.6053. ⟨10.3390/molecules26196053⟩. ⟨hal-03418904⟩
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