Chemoselective Formation of Successive Triazole Linkages in One Pot: “Click−Click” Chemistry
- 1 September 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (20) , 4505-4507
- https://doi.org/10.1021/ol061657d
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.Keywords
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