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 |
|---|---|
| Pages (from-to) | 7030-7032 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 49 |
| Issue number | 49 |
| DOIs | |
| State | Published - Dec 1 2008 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry
- Drug Discovery
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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 journal › Article
}
TY - JOUR
T1 - Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene
AU - Fletcher, James T.
AU - Walz, Sara E.
AU - Keeney, Matthew E.
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.
UR - http://www.scopus.com/inward/record.url?scp=54049111317&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=54049111317&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2008.09.136
DO - 10.1016/j.tetlet.2008.09.136
M3 - Article
AN - SCOPUS:54049111317
VL - 49
SP - 7030
EP - 7032
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 49
ER -