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

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 coppe...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2004; no. 18; pp. 3789 - 3791
Main Authors Jin, T, Kamijo, S, Yamamoto, Y
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.09.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TETRAZOLES
PHASE
cycloaddition
AZIDES
alkynes
copper
catalysis
EFFICIENT
1,2,3-triazoles
TRIAZOLES
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Summary: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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.20040442