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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-00387909
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Submitted on : Tuesday, May 26, 2009 - 10:01:30 AM
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Vincent Aucagne, David A. Leigh. Chemoselective formation of successive triazole linkages in one pot: "click-click" chemistry. Organic Letters, American Chemical Society, 2006, 8 (20), pp.4505-4507. ⟨10.1021/ol061657d⟩. ⟨hal-00387909⟩

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