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Double Regioselective Thermal Azide-Alkyne Cycloaddition of 1,3-Diynes.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2024 May 03; Vol. 89 (9), pp. 6527-6532. Date of Electronic Publication: 2024 Apr 19. - Publication Year :
- 2024
-
Abstract
- A double regioselective cycloaddition reaction of 1,3-diynes with azide is reported to synthesize fully substituted 5-alkynyl-1,2,3-triazoles without any catalyst, metal, or other factor. Computational studies revealed that the 5-alkynyl-1,2,3-triazole derivative is both kinetically and thermodynamically favorable irrespective of the nature of the substituents at the alkyne termini in 1,3-diynes. The simplicity of the reaction, extremely high regioselectivity under metal-free conditions, wide substrate scope, and good to excellent yields might inspire further studies of the cycloaddition of 1,3-diynes in addition to click chemistry.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 89
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38639379
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00010