Acid Switchable Reaction of CF 3 -Ynones with Hydroxylamine To Form Selectively 3- and 5-CF 3 -Isoxazoles
Abstract
Efficient regioselective one-pot approaches toward 5- and 3-CF 3 -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 3 -isoxazoles are formed while 5-CF 3 -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.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Synthesis and Characterization of Pyrroles
Sulfur-Based Synthesis Techniques
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 8
- Pages
- 3196–3207
- Publication date
- 12 February 2026
- Language
- EN