Expedient Azide-Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO4 with Cu(0) in Aqueous Media.

ABSTRACT

A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl ß-azido glycosides with three different terminal alkynes in CH3CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected ß-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.