Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes

Tetsuo Kin; Shin Kamijo; Yoshinori Yamamoto

doi:10.1002/ejoc.200400442

Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes

Tetsuo Kin, Shin Kamijo, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

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

173 Citations (Scopus)

Abstract

The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of Cu^I catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction.

Original language	English
Pages (from-to)	3789-3791
Number of pages	3
Journal	European Journal of Organic Chemistry
Issue number	18
DOIs	https://doi.org/10.1002/ejoc.200400442
Publication status	Published - 2004 Sept 13

Keywords

1,2,3-Triazoles
Alkynes
Catalysis
Copper
Cycloaddition

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200400442

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AU - Kin, Tetsuo

AU - Kamijo, Shin

AU - Yamamoto, Yoshinori

PY - 2004/9/13

Y1 - 2004/9/13

N2 - The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction.

AB - The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction.

KW - 1,2,3-Triazoles

KW - Alkynes

KW - Catalysis

KW - Copper

KW - Cycloaddition

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ER -

Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes

Abstract

Keywords

ASJC Scopus subject areas

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