Journal
TETRAHEDRON LETTERS
Volume 49, Issue 49, Pages 7030-7032Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.09.136
Keywords
Click chemistry; 1,2,3-Triazoles; One-pot reaction
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Funding
- Research Corporation Cottrell College Science [CC6349]
- Creighton University
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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. (C) 2008 Elsevier Ltd. All rights reserved.
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