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

Ebbe Engholm; sgz228 sgz228; Klas Ola Blixt

doi:10.1016/j.tetlet.2017.04.095

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

Ebbe Engholm, sgz228 sgz228, Klas Ola Blixt^*

^*Corresponding author for this work

Department of Chemistry

5 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Tetrahedron Letters
Volume	58
Issue number	23
Pages (from-to)	2272-2275
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2017.04.095
Publication status	Published - 7 Jun 2017

Keywords

1,4.5-Substituted 1,2,3-triazoles
1,5-Substituted 1,2,3-triazoles
Ruthenium catalysts
Ruthenium-assisted azide-alkyne cycloaddition
Side-chain protected peptides

Access to Document

10.1016/j.tetlet.2017.04.095

Cite this

@article{168e2e81cdb248d0b824251668502e7d,

title = "Facile solid-phase ruthenium assisted azide-alkyne cycloaddition (RuAAC) utilizing the Cp*RuCl(COD)-catalyst",

abstract = "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.",

keywords = "1,4.5-Substituted 1,2,3-triazoles, 1,5-Substituted 1,2,3-triazoles, Ruthenium catalysts, Ruthenium-assisted azide-alkyne cycloaddition, Side-chain protected peptides",

author = "Ebbe Engholm and sgz228 sgz228 and Blixt, {Klas Ola}",

year = "2017",

month = jun,

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doi = "10.1016/j.tetlet.2017.04.095",

language = "English",

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journal = "Tetrahedron Letters",

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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