Work

Radical Rearrangement of Terminal Epoxides to Methyl Ketones via Cobalt Photocatalysis

Year: 2026

Type: article

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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c01341

Authors: Brian Funk, Michael Yasuda, Julian G. West

Institution: Rice University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Welch Foundation, Research Corporation for Science Advancement, National Institutes of Health, National Institute of General Medical Sciences