Reactivity of 2<i>H</i>-Azirines in Copper-Catalyzed Azide–Alkyne Cycloaddition Reactions
A reaction between azide, alkyne and 2<i>H</i>-azirine resulted in C-C bond formation at position five of 1,2,3-triazole, instead of previously misidentified C-N bond connectivity. The reaction mechanism of this C-C bond formation on the triazole ring was fully explained by employing calibrated QM(DFT-D3) calculations. Functionalization of primary products provided substituted pyrimidine, furan or 1,3-oxazepine.
Authors
- Petr Beier (ORCID: https://orcid.org/0000-0002-0888-7465)
- Lukáš Janecký (ORCID: https://orcid.org/0000-0002-9310-6423)
- Blanka Klepetářová (ORCID: https://orcid.org/0000-0003-3916-7839)
- Andrea Madabeni
- Lubomı́r Rulı́šek (ORCID: https://orcid.org/0000-0002-7769-7059)
- Eliška Jelínková
Institutions
- Charles University (CZ)
- Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry (CZ)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-01
- DOI
- https://doi.org/10.1021/acs.orglett.5c03150
- Citations
- 2
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Ministerstvo Školství, Mládeže a Tělovýchovy
- Grantová Agentura České Republiky
- Akademie Věd České Republiky
- Ústav organické chemie a biochemie Akademie věd České republiky