RuCl2(PPh3)3-catalyzed transfer hydrogenation of Image-glucose

Abstract

Glucose is transfer hydrogenated by propan-2-ol, butan-2-ol, cyclohexanol, benzyl alcohol, 1-phenylethanol, benzhydrol, 2-methoxyethanol and tetrahydrofurfuryl alcohol in the presence of RuCl2(PPh3)3 at 100 °C and atmospheric pressure. Mixed solvent systems such as dimethylacetamide-water and dioxane-water are utilized for this reaction. The major product from glucose is sorbitol, although glucono-1,5-lactone is invariably formed as a side product from a disproportionation reaction. When 2-methoxyethanol and tetrahydrofurfuryl alcohol are used as hydrogen donors, the catalyst undergoes permanent change to a hydridocarbonyl complex, which catalyzes only disproportionation of glucose. Glucose also acts as a good hydrogen donor when hydrogen acceptors such as cyclohexanone are introduced into the reaction system.