Related Experiment Video
Updated: May 12, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Radical Rearrangement of Terminal Epoxides to Methyl Ketones via Cobalt Photocatalysis
Brian Funk1, Michael Yasuda1, Julian G West1
1Department of Chemistry, Rice University, 6100 Main St MS 602, Houston, Texas 77005, United States.
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.
Related Concept Videos
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Radical Formation: Elimination
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
Acid-Catalyzed Ring-Opening of Epoxides
