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DOI: 10.1055/s-2005-921919
Copper(I)-Mediated Synthesis of Trisubstituted 1,2,3-Triazoles
Publication History
Publication Date:
28 November 2005 (online)
Abstract
A copper-catalysed coupling of bromo-alkynes and organic azides is described. This coupling results in the formation of bromo-containing trisubstituted 1,2,3-triazole derivatives in high yield and a regioselective manner.
Key words
1,4,5-trisubstituted-1,2,3-triazole - click reaction - [3+2] dipolar cycloaddition - Cu-catalysis - glycopeptide
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References
The regiochemistry was determined via reduction to the 5-hydrogen-1,2,3-triazole, using i-PrMgCl and subsequent quenching with MeOH, followed by comparison to the known 1,4-disubstituted triazole.
11Heating of the reaction mixture to temperatures higher than 50 °C led to the formation of small amounts of the 1,5-regioisomer, which was probably formed via a thermal [3+2] cycloaddition.