1,3-Dipolar Cycloaddition of SF<sub>5</sub>-Alkynes with Nonstabilized Diazo: Synthesis of Highly Substituted SF<sub>5</sub>-3<i>H</i>-Pyrazoles
This work presents the 1,3-dipolar cycloaddition of SF<sub>5</sub>-alkynes with nonstabilized diazo compounds under mild conditions, producing highly substituted SF<sub>5</sub>-3<i>H</i>-pyrazoles. Eighteen examples are given, with yields of up to 91%. The two regioisomers were obtained in ratios ranging from 27:73 to 73:27. The products can undergo a Van Alphen-Huttel rearrangement. DFT calculations were performed to understand the selectivities and rearrangements.
Authors
- André B. Charette (ORCID: https://orcid.org/0000-0001-5622-5063)
- Laurent Vinet (ORCID: https://orcid.org/0000-0001-9390-1235)
- Lauriane C. Peyrical (ORCID: https://orcid.org/0000-0003-4359-8877)
- Emna Azek
Institutions
- Centre in Green Chemistry and Catalysis (CA)
- Université de Montréal (CA)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c04200
- Citations
- 6
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Canada Foundation for Innovation
- Université de Montréal
- Natural Sciences and Engineering Research Council of Canada
- Fonds de recherche du Québec – Nature et technologies