Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene

James T. Fletcher; Sara E. Walz; Matthew E. Keeney

doi:10.1016/j.tetlet.2008.09.136

Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene

James T. Fletcher, Sara E. Walz, Matthew E. Keeney

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal yields of the desired products. The reaction conditions were found to be successful for both alkyl and aryl azide reactants, including analogs with electron-donating and electron-withdrawing functionality. This procedure stands as a simple and regioselective means by which to prepare 1-substituted-1,2,3-triazole compounds directly from azide precursors.

Original language	English (US)
Pages (from-to)	7030-7032
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2008.09.136
State	Published - Dec 1 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene",

abstract = "Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal yields of the desired products. The reaction conditions were found to be successful for both alkyl and aryl azide reactants, including analogs with electron-donating and electron-withdrawing functionality. This procedure stands as a simple and regioselective means by which to prepare 1-substituted-1,2,3-triazole compounds directly from azide precursors.",

author = "Fletcher, {James T.} and Walz, {Sara E.} and Keeney, {Matthew E.}",

note = "Funding Information: J.T.F. acknowledges the Research Corporation Cottrell College Science Award Program (CC6349) and Creighton University for financial support. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

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AU - Fletcher, James T.

AU - Walz, Sara E.

AU - Keeney, Matthew E.

N1 - Funding Information: J.T.F. acknowledges the Research Corporation Cottrell College Science Award Program (CC6349) and Creighton University for financial support. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2008/12/1

Y1 - 2008/12/1

N2 - Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal yields of the desired products. The reaction conditions were found to be successful for both alkyl and aryl azide reactants, including analogs with electron-donating and electron-withdrawing functionality. This procedure stands as a simple and regioselective means by which to prepare 1-substituted-1,2,3-triazole compounds directly from azide precursors.

AB - Two-step one-pot reaction conditions have been developed for synthesizing 1-substituted-1,2,3-triazoles. This transformation involves the base-catalyzed deprotection of trimethylsilylacetylene followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition under aqueous reaction conditions. Utilization of potassium carbonate as the base and methanol as the alcoholic aqueous co-solvent resulted in optimal yields of the desired products. The reaction conditions were found to be successful for both alkyl and aryl azide reactants, including analogs with electron-donating and electron-withdrawing functionality. This procedure stands as a simple and regioselective means by which to prepare 1-substituted-1,2,3-triazole compounds directly from azide precursors.

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Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene

Abstract

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