TY - JOUR
T1 - Facile solid-phase ruthenium assisted azide-alkyne cycloaddition (RuAAC) utilizing the Cp*RuCl(COD)-catalyst
AU - Engholm, Ebbe
AU - sgz228, sgz228
AU - Blixt, Klas Ola
PY - 2017/6/7
Y1 - 2017/6/7
N2 - 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 1h.
AB - 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 1h.
KW - 1,4.5-Substituted 1,2,3-triazoles
KW - 1,5-Substituted 1,2,3-triazoles
KW - Ruthenium catalysts
KW - Ruthenium-assisted azide-alkyne cycloaddition
KW - Side-chain protected peptides
U2 - 10.1016/j.tetlet.2017.04.095
DO - 10.1016/j.tetlet.2017.04.095
M3 - Journal article
SN - 0040-4039
VL - 58
SP - 2272
EP - 2275
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 23
ER -