《Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed In Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles》 was written by Jankovic, Dominik; Virant, Miha; Gazvoda, Martin. Application of 510758-28-8This research focused ontriazole preparation green chem; azide alkyne cycloaddition copper. The article conveys some information:
Authors report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analog of losartan. The preparation of orthogonally protected azahistidine from Fmoc-L-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in <6% concentrations at which it is safe to handle. Reactions of distilled solutions of hydrazoic acid indicated its role as a reactive species in the copper-catalyzed reaction. In the part of experimental materials, we found many familiar compounds, such as Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8Application of 510758-28-8)
Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8) is a polytriazolylamine ligand which stabilizes Cu(I) towards disproportionation and oxidation thus enhancing its catalytic effect in the azide-acetylene cycloaddition.Application of 510758-28-8
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics