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

Overview

Journal ACS Org Inorg Au

Publisher American Chemical Society

Date 2024 Apr 8

PMID 38585512

Authors

Wen-Chieh Yang

Chien-Tien Chen

Affiliations

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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 β-azido glycosides with three different terminal alkynes in CHCN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.

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