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Copper‐Catalyzed Synthesis of N ‐Unsubstituted 1,2,3‐Triazoles from Nonactivated Terminal Alkynes
Author(s) -
Jin Tienan,
Kamijo Shin,
Yamamoto Yoshinori
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400442
Subject(s) - chemistry , acetylide , cycloaddition , hydrazoic acid , catalysis , copper , azide , medicinal chemistry , terminal (telecommunication) , trimethylsilyl azide , trimethylsilyl , organic chemistry , telecommunications , computer science
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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