Radical Rearrangement of Terminal Epoxides to Methyl Ketones via Cobalt Photocatalysis
Abstract
The acid-catalyzed Meinwald rearrangement of epoxides is a powerful and economical method for generating carbonyl compounds, but regioselectivity is dominated by carbocation stability. Herein, we report a redox-neutral and highly selective cobaloxime-photocatalyzed protocol for the isomerization of terminal epoxides to methyl ketones under visible-light irradiation. This system provides complementary products to the Meinwald rearrangement under mildly basic conditions and exhibits broad functional group tolerance. Additionally, preliminary investigations suggest it proceeds through a radical mechanism.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 20
- Pages
- 6281–6286
- Publication date
- 11 May 2026
- Language
- EN