Synthesis of Triazoles from Nonactivated Terminal Alkynes via the Three-Component Coupling Reaction Using a Pd(0)−Cu(I) Bimetallic Catalyst

Shin Kamijo,† Tienan Jin,‡ Zhibao Huo,‡ and Yoshinori Yamamoto*‡
Research Center for Sustainable Materials Engineering, Institute of Multidisciplinary Research for Advanced Materials, and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
J. Am. Chem. Soc., 2003, 125 (26), pp 7786–7787
DOI: 10.1021/ja034191s
Publication Date (Web): June 6, 2003
Copyright © 2003 American Chemical Society
†

 Institute of Multidisciplinary Research for Advanced Materials.

,
‡

 Department of Chemistry.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, yoshi@yamamoto1.chem.tohoku.ac.jp

Abstract

Abstract Image

The synthesis of triazoles via the three-component coupling reaction of unactivated terminal alkynes, allyl carbonate, and trimethylsiyl azide under the Pd(0)−Cu(I) bimetallic catalyst is developed. The reaction most probably proceeds through the formation of a π-allylpalladium azide complex and a copper-acetylide followed by a successive [3 + 2] cycloaddition. The deallylation of the resulting allyltriazoles proceeds very easily by the Ru-catalyzed isomerization followed by the ozonolysis of the resulting propenyltriazoles to give the triazoles in high yields.

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History

  • Published In Issue July 02, 2003
  • Received January 16, 2003

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