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

Wen-Chieh Yang; Chien-Tien Chen

doi:10.1021/acsorginorgau.3c00059

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

ACS Org Inorg Au. 2023 Dec 19;4(2):235-240. doi: 10.1021/acsorginorgau.3c00059. eCollection 2024 Apr 3.

Authors

Wen-Chieh Yang¹, Chien-Tien Chen¹

Affiliation

¹ Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang-Fu Road, Hsinchu 30013, Taiwan R.O.C.

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 CH₃CN. 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.