Synthesis of (4-Trifluoromethyl)isoxazoles through a Tandem Trifluoromethyloximation/Cyclization/Elimination Reaction of α,β-Unsaturated Carbonyls

Paramita Pattanayak and Tanmay Chatterjee*

*Department of Chemistry, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500078, Telangana, India, Email: tanmayhyderabad.bits-pilani.ac.in

P. Pattanayak, T. Chatterjee, J. Org. Chem., 2023, 88, 5420-5430.

DOI: 10.1021/acs.joc.2c03053

---

see article for more reactions

Abstract

A metal-free, cascade regio- and stereoselective trifluormethyloximation, cyclization, and elimination strategy of readily available α,β-unsaturated carbonyl compounds with CF₃SO₂Na and tBuONO provides a wide variety of 4-(trifluoromethyl)isoxazoles. Mechanistic studies revealed a radical pathway for the reaction.

see article for more examples

proposed mechanism

---

---

Key Words

isoxazoles, trifluoromethylation, tBuONO, multicomponent reactions

---

ID: J42-Y2023