Gold-Catalyzed Oxidative Transformation ...
Document type :
Article dans une revue scientifique: Article original
Permalink :
Title :
Gold-Catalyzed Oxidative Transformation of Free Sugars into Biobased Platform Molecules
Author(s) :
Quéhon, Lucie [Auteur]
Sauvage, Frédéric [Auteur]
Ahouari, Hania [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Golonu, Sema [Auteur]
Vezin, Herve [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516
Wadouachi, Anne [Auteur]
Pourceau, Gwladys [Auteur]
Sauvage, Frédéric [Auteur]
Ahouari, Hania [Auteur]

Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Golonu, Sema [Auteur]
Vezin, Herve [Auteur]

Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516
Wadouachi, Anne [Auteur]
Pourceau, Gwladys [Auteur]
Journal title :
ACS Sustainable Chemistry & Engineering
Abbreviated title :
ACS Sustainable Chem. Eng.
Volume number :
11
Pages :
11041-11051
Publisher :
American Chemical Society (ACS)
Publication date :
2023-07-20
ISSN :
2168-0485
English keyword(s) :
sugar lactones
gold-catalyzed oxidation
transformation of free sugars
gold-catalyzed oxidation
transformation of free sugars
HAL domain(s) :
Chimie
Chimie/Chimie théorique et/ou physique
Chimie/Chimie théorique et/ou physique
English abstract : [en]
Due to their easy conversion into high-added value products, sugar lactones and their derivatives are very attractive biobased platform molecules. Yet, conventional transformation of free sugars into such activated compounds ...
Show more >Due to their easy conversion into high-added value products, sugar lactones and their derivatives are very attractive biobased platform molecules. Yet, conventional transformation of free sugars into such activated compounds is not so handy: a multistep procedure requiring protection/oxidation/lactonization-esterification/deprotection is often necessary. We report herein a procedure allowing one to rapidly and efficiently form lactones/esters directly from free sugars under mild conditions, catalyzed with a small amount (0.36 mol %) of recyclable gold nanocatalyst under oxygen atmosphere. The conditions were optimized using galactose as a model, quantitatively and selectively affording 1,4-galactonolactone in 2 h at room temperature. The procedure was then successfully applied to a variety of hexoses and pentoses leading to excellent conversion (>86%). Due to the equilibrium between lactone regioisomers and ester forms, a mixture of 1,4-lactone, 1,5-lactone and methyl ester can be generally obtained depending on the sugar series. A subsequent reaction of the crudes with benzylamine leads to a total conversion of lactones/esters into corresponding amides, confirming the efficiency of the procedure and paving the way to a one-pot transformation of free sugars into high added value sugar-based derivatives. Based on NMR and ESR analyses, a mechanism of the reaction involving CH3O• radical species seems to be taking shape.Show less >
Show more >Due to their easy conversion into high-added value products, sugar lactones and their derivatives are very attractive biobased platform molecules. Yet, conventional transformation of free sugars into such activated compounds is not so handy: a multistep procedure requiring protection/oxidation/lactonization-esterification/deprotection is often necessary. We report herein a procedure allowing one to rapidly and efficiently form lactones/esters directly from free sugars under mild conditions, catalyzed with a small amount (0.36 mol %) of recyclable gold nanocatalyst under oxygen atmosphere. The conditions were optimized using galactose as a model, quantitatively and selectively affording 1,4-galactonolactone in 2 h at room temperature. The procedure was then successfully applied to a variety of hexoses and pentoses leading to excellent conversion (>86%). Due to the equilibrium between lactone regioisomers and ester forms, a mixture of 1,4-lactone, 1,5-lactone and methyl ester can be generally obtained depending on the sugar series. A subsequent reaction of the crudes with benzylamine leads to a total conversion of lactones/esters into corresponding amides, confirming the efficiency of the procedure and paving the way to a one-pot transformation of free sugars into high added value sugar-based derivatives. Based on NMR and ESR analyses, a mechanism of the reaction involving CH3O• radical species seems to be taking shape.Show less >
Language :
Anglais
Peer reviewed article :
Oui
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
Université de Lille
CNRS
CNRS
Collections :
Research team(s) :
Propriétés magnéto structurales des matériaux (PMSM)
Submission date :
2023-09-19T11:31:31Z
2023-09-21T14:36:44Z
2023-09-21T14:36:44Z
Files
- acssuschemeng.3c00975.pdf
- Version éditeur
- Restricted access
- Access the document