Practical Site-Selective Oxidation of Glycosides with Palladium(II) Acetate/Neocuproine

Synlett DOI: 10.1055/a-2186-1485 The palladium-catalyzed oxidation of the secondary C(3) hydroxy group of glycopyranosides has set a mark in the selective modification of unprotected carbohydrates. The preformed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes di- and oligosaccharides, as well as monosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd catalyst is formed in situ from Pd(OAc)2 and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol was applied to a series of mono- and disaccharides, and has been applied on a 10 gram scale. The protocol is also valuable as a screening method to determine whether more-extensive studies using the preformed catalyst are worthwhile. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  open access Full text
Source: Synlett - Category: Chemistry Authors: Tags: cluster Source Type: research