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

64 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

Access to Document

10.1016/j.tetlet.2008.09.136

Cite this

@article{53fb91dfc894433db0c619a047f2786c,

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. ",

year = "2008",

month = dec,

day = "1",

doi = "10.1016/j.tetlet.2008.09.136",

language = "English (US)",

volume = "49",

pages = "7030--7032",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "49",

}

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.

N1 - Funding Information: J.T.F. acknowledges the Research Corporation Cottrell College Science Award Program (CC6349) and Creighton University for financial support.

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 -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this