Copper(I)-Catalyzed Cycloaddition of Bismuth(III) Acetylides with Organic Azides: Synthesis of Stable Triazole Anion Equivalents

摘要

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC; Scheme la) is now widely used as a reliable method for covalently connecting diverse building blocks. The experimental simplicity of the reaction and the robust nature of 1,2,3-triazole products have enabled numerous applications of this process in synthetic and medicinal chemistry, bioconjugations, material science, and polymer chemistry. The recent discovery that 1-iodoalkynes also readily react with organic azides, regiospecifically producing 5-iodo-1,2,3-triazoles (Scheme lb), further expanded the utility of this copper-catalyzed reaction.