We thank the University of Leuven and the FWO-Vlaanderen for financial support. The Erasmus Exchange program “Experts II” is acknowledged for a fellowship to N.P.
A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles†
Article first published online: 2 JUL 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 38, pages 10155–10159, September 15, 2014
How to Cite
Thomas, J., John, J., Parekh, N. and Dehaen, W. (2014), A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles. Angew. Chem. Int. Ed., 53: 10155–10159. doi: 10.1002/anie.201403453
- Issue published online: 9 SEP 2014
- Article first published online: 2 JUL 2014
- Manuscript Revised: 12 MAY 2014
- Manuscript Received: 18 MAR 2014
- University of Leuven
- dipolar cycloaddition;
- multicomponent reactions;
A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks, such as aldehydes, nitroalkanes, and organic azides, is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound, which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope, and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.