Highly efficient Cu(acac)2 catalyzed multi component synthesis of 1,4-dis-ubstituted-1,2,3-triazoles using aryl halide/ phenyl boronic acid or styrene oxide and aryl alkynes with sodium azide in aqueous medium

The sequential three-component reaction of aryl halide/phenyl boronic acid or styrene oxide, with sodium azide and alkynes using copper catalysis has been discussed. The reaction proceeds via the in-situ generation of aryl azide/azido-alcohol followed by synthesis of 1,4-disubstituted-1,2,3-triazole...

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Bibliographic Details
Published inTetrahedron Vol. 179
Main Authors Pappula, Upendra, Kalyana, Venkata Prasad, Roy, Ujjal Kanti
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.07.2025
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Aryl halide activation
COPPER NANOPARTICLES
ONE-POT
CLICK CHEMISTRY
COMPLEXES
Copper catalyst
3+2 CYCLOADDITION
Cycloaddition
4-Disubstituted-1
3-triazoles
beta-Hydroxy-triazoles
1,2,3-TRIAZOLES
IN-SITU
1,4-DISUBSTITUTED-1,2,3-TRIAZOLES
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Summary:The sequential three-component reaction of aryl halide/phenyl boronic acid or styrene oxide, with sodium azide and alkynes using copper catalysis has been discussed. The reaction proceeds via the in-situ generation of aryl azide/azido-alcohol followed by synthesis of 1,4-disubstituted-1,2,3-triazoles/beta-hydroxy-triazoles. Relatively inert aryl halides are smoothly activated by the catalyst to form aryl azide sin situ. The multicomponent approach of the reaction makes it efficient, easy to perform and variety of functional group tolerant. This copper-catalyzed aqueous [3 + 2] azide-alkyne cycloaddition (CuAAC) reactions of in situ generated aryl azide/azido-alcohol and alkyne using commercially and readily available Cu(acac)2 catalyst serves as an efficient protocol in "Click Chemistry''.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2025.134629