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

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

Research output: Contribution to journalArticle

54 Citations (Scopus)

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 languageEnglish
Pages (from-to)7030-7032
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number49
DOIs
StatePublished - Dec 1 2008

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Triazoles
Azides
Electrons
Cycloaddition
Cycloaddition Reaction
Methanol
potassium carbonate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene. / Fletcher, James T.; Walz, Sara E.; Keeney, Matthew E.

In: Tetrahedron Letters, Vol. 49, No. 49, 01.12.2008, p. 7030-7032.

Research output: Contribution to journalArticle

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