Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars

Frédéric   Sauvage; Yan Busby; Mehdi Omri; Matthieu Becuwe; Gwladys Pourceau; Anne Wadouachi

doi:10.1021/acscatal.7b03394

Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars

Frédéric Sauvage, Yan Busby, Mehdi Omri, Matthieu Becuwe, Gwladys Pourceau, Anne Wadouachi

Namur Institute of Structured Matter

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Abstract

A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003-0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al ₂O ₃, Au/TiO ₂, and Au/CeO ₂, the latter being the most efficient (TOF > 750 000 h ^-1) and perfectly selective. Only a 10 min exposition under standard incident sunlight irradiation (A.M.1.5G conditions, 100 mW/cm ²) affords total conversion of glucose into the corresponding sodium gluconate. Demonstrating its versatility, this methodology was successfully applied to a variety of oligosaccharides leading to the corresponding aldonates in quantitative yield and high purity (>95%) without any purification step. The photocatalyst was recovered by simple filtration and reused 5 times leading to the same conversion and selectivity after 10 min of illumination.

Original language	English
Pages (from-to)	1635-1639
Number of pages	5
Journal	ACS Catalysis
Volume	8
Issue number	3
DOIs	https://doi.org/10.1021/acscatal.7b03394
Publication status	Published - 2 Mar 2018

Keywords

carbohydrates
photocatalytic oxidation
gold catalysis
aldonates
oligosaccharides modification

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title = "Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars",

abstract = "A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003-0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al 2O 3, Au/TiO 2, and Au/CeO 2, the latter being the most efficient (TOF > 750 000 h -1) and perfectly selective. Only a 10 min exposition under standard incident sunlight irradiation (A.M.1.5G conditions, 100 mW/cm 2) affords total conversion of glucose into the corresponding sodium gluconate. Demonstrating its versatility, this methodology was successfully applied to a variety of oligosaccharides leading to the corresponding aldonates in quantitative yield and high purity (>95%) without any purification step. The photocatalyst was recovered by simple filtration and reused 5 times leading to the same conversion and selectivity after 10 min of illumination. ",

keywords = "carbohydrates, photocatalytic oxidation, gold catalysis, aldonates, oligosaccharides modification",

author = "Fr{\'e}d{\'e}ric Sauvage and Yan Busby and Mehdi Omri and Matthieu Becuwe and Gwladys Pourceau and Anne Wadouachi",

note = "Funding Information: M.O., M.B., G.P., and A.W. wish to thank the Conseil Reǵ ional de Picardie for its financial support. F.S. acknowledges the French National Research Agency (ANR) for funding Photo2-batt project. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acscatal.7b03394",

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T2 - A Fast and Selective Procedure for the Oxidation of Free Sugars

AU - Sauvage, Frédéric

AU - Busby, Yan

AU - Omri, Mehdi

AU - Becuwe, Matthieu

AU - Pourceau, Gwladys

AU - Wadouachi, Anne

N1 - Funding Information: M.O., M.B., G.P., and A.W. wish to thank the Conseil Reǵ ional de Picardie for its financial support. F.S. acknowledges the French National Research Agency (ANR) for funding Photo2-batt project. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/3/2

Y1 - 2018/3/2

N2 - A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003-0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al 2O 3, Au/TiO 2, and Au/CeO 2, the latter being the most efficient (TOF > 750 000 h -1) and perfectly selective. Only a 10 min exposition under standard incident sunlight irradiation (A.M.1.5G conditions, 100 mW/cm 2) affords total conversion of glucose into the corresponding sodium gluconate. Demonstrating its versatility, this methodology was successfully applied to a variety of oligosaccharides leading to the corresponding aldonates in quantitative yield and high purity (>95%) without any purification step. The photocatalyst was recovered by simple filtration and reused 5 times leading to the same conversion and selectivity after 10 min of illumination.

AB - A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003-0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al 2O 3, Au/TiO 2, and Au/CeO 2, the latter being the most efficient (TOF > 750 000 h -1) and perfectly selective. Only a 10 min exposition under standard incident sunlight irradiation (A.M.1.5G conditions, 100 mW/cm 2) affords total conversion of glucose into the corresponding sodium gluconate. Demonstrating its versatility, this methodology was successfully applied to a variety of oligosaccharides leading to the corresponding aldonates in quantitative yield and high purity (>95%) without any purification step. The photocatalyst was recovered by simple filtration and reused 5 times leading to the same conversion and selectivity after 10 min of illumination.

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Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars

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