Oxa-π,σ‑Methane Rearrangement for Epoxide Construction via Energy-Transfer Catalysis

Keywords

epoxides - energy-transfer catalysis - 9H-thioxanthen-9-one - TXT - radicals

Significance

The authors report an oxa- π, σ-methane rearrangement to generate epoxides. This strategy relies on energy-transfer catalysis to generate the diradical species, which undergoes a series of transformations leading to the final radical–radical coupling step, giving rise to valuable epoxides in excellent yields and good functional group tolerance.

Comment

Epoxides represent a versatile functional group in synthetic chemistry. However, typical synthetic pathways mainly rely on oxidation of alkenes or formation from carbonyl compounds. Here, the authors present a creative strategy expanding the scope, relying only on an organic photosensitizer and eliminating the need for metals or strong oxidants.

Publication History

Article published online:
22 May 2025