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

Wen-Chieh YangChien-Tien Chen
ACS Organic and Inorganic Au
01/03/2024

摘要

1,3-dipolar cycloaddition;1,4-disubstituted triazoles;green chemistry;thiol-compatible;vanadyl species Physical and Theoretical Chemistry Organic Chemistry Inorganic Chemistry

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 CH 3 CN. 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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https://doi.org/10.1021/acsorginorgau.3c00059檢視
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