Facile solid-phase ruthenium assisted azide-alkyne cycloaddition (RuAAC) utilizing the Cp∗RuCl(COD)-catalyst

Add time:09/09/2019    Source:sciencedirect.com

The ruthenium assisted azide-alkyne cycloaddition (RuAAC) reaction is a well-established method for the generation of 1,5- and 1,4,5-substituted 1,2,3-triazoles, which we have extended to the solid-phase synthesis of 1,2,3-triazole-peptides. The 1,2,3-triazole moieties were formed upon the reaction of alkynes with a solid-phase bound secondary azide in the presence of the Cp∗RuCl(COD) catalyst at room temperature. Both terminal and internal alkynes underwent highly regioselective cycloaddition reactions under mild conditions, facilitating release of the peptide construct from the resin with intact side-chain protection. Almost quantitative conversion to the corresponding 1,2,3-triazoles was observed within 1 h.

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