Acid Switchable Reaction of CF <sub>3</sub> -Ynones with Hydroxylamine To Form Selectively 3- and 5-CF <sub>3</sub> -Isoxazoles
Efficient regioselective one-pot approaches toward 5- and 3-CF<sub>3</sub>-isoxazoles were elaborated using reaction of hydroxylamine and its hydrochloride in ethanol. The reaction direction is easily switched by the acidity of the reaction media. In acidic conditions 3-CF<sub>3</sub>-isoxazoles are formed while 5-CF<sub>3</sub>-isoxazoles can be synthesized in basic media. High (up to 99%) yields, mild conditions, and simplicity of the reaction protocol are the advantages of the proposed methods. The reaction mechanism and regioselectivity were explained by DFT calculations.
Authors
- M. S. Nechaev
- Vasiliy M. Muzalevskiy
- Valentine G. Nenajdenko
Institutions
- Russian Academy of Sciences (RU)
- Lomonosov Moscow State University (RU)
- A.V. Topchiev Institute of Petrochemical Synthesis (RU)
- Moscow State University (TJ)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-02-12
- DOI
- https://doi.org/10.1021/acs.joc.5c02908
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00