Chemoselective formation of successive triazole linkages in one pot: "click-click" chemistry

Vincent Aucagne (1) , David A. Leigh

1 School of Chemistry, University of Edinburgh

A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical "click" chemistry.

Domaines: Chimie organique

Vincent Aucagne, David A. Leigh. Chemoselective formation of successive triazole linkages in one pot: "click-click" chemistry. Organic Letters, 2006, 8 (20), pp.4505-4507. ⟨10.1021/ol061657d⟩. ⟨hal-00387909⟩