C-Aryl Glycosylation: Palladium-Catalyzed Aryl–Allyl Coupling of Achmatowicz Rearrangement Products with Arylboronic Acids
Ming Wai Liaw, Wai Fung Cheng, Rongbiao Tong
Abstract
The first Pd-catalyzed arylation of Achmatowicz rearrangement products with arylboronic acids under mild conditions (rt) to provide the synthetically versatile C-aryl dihydropyranones is reported. It is found that the 4-keto group of Achmatowicz products is essential to increase the reactivity of the Pd-π-allyl complex toward arylboronic acids and that phosphine as the palladium ligand would be destructive to the reaction. This new coupling method addresses the major limitations of previous Pd-catalyzed allyl-aryl couplings of 2,3-unsaturated glycosides with an aryl Grignard or aryl zinc reagent.
Topics & Concepts
ChemistryArylPalladiumPhosphineCatalysisReagentLigand (biochemistry)Combinatorial chemistryOrganic chemistryMedicinal chemistryAlkylBiochemistryReceptorCarbohydrate Chemistry and SynthesisSynthesis and Biological ActivitySynthesis of Organic Compounds