Abstract
A new method of azide-alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
| Original language | English |
|---|---|
| Pages (from-to) | 978-985 |
| Number of pages | 8 |
| Journal | Organic Chemistry Frontiers |
| Volume | 4 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 1 Jun 2017 |
ASJC Scopus subject areas
- Organic Chemistry
Fingerprint Dive into the research topics of 'Regioselective Zn(OAc)<sub>2</sub>-catalyzed azide-alkyne cycloaddition in water: The green click-chemistry'. Together they form a unique fingerprint.
Cite this
Morozova, M. A., Yusubov, M. S., Kratochvil, B., Eigner, V., Bondarev, A. A., Yoshimura, A., Saito, A., Zhdankin, V. V., Trusova, M. E., & Postnikov, P. S. (2017). Regioselective Zn(OAc)2-catalyzed azide-alkyne cycloaddition in water: The green click-chemistry. Organic Chemistry Frontiers, 4(6), 978-985. https://doi.org/10.1039/c6qo00787b