Work

Photochemical Radical Ring-Opening Alkylation of Cyclopropanols with Katritzky Salts

Year: 2025

Type: article

Abstract: Ring-cleavage reactions of cyclopropyl alcohols are a valuable tool for the synthesis of linear and α- or β-branched ketones. Here, we describe a visible light-induced ring-opening alkylation of these substrates with benzyl, allyl, and secondary alkyl Katritzky salts. The reaction proceeds under dual photoredox and nickel catalysis in the presence of a titanium(IV) isopropoxide additive. Mechanistically, the ring-opening step starts with generation of the cyclopropoxy radical and is followed by its isomerization to the β-carbonyl radical. This enables the regioselective preparation of β-branched ketones from 1,2-disubstituted hydroxycyclopropanes.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04556

Authors: Ulada Karotsina, Kirill Stasko, Vitaly Syakhovich, Ivan Lysenko, Alaksiej Hurski

Institutions: National Academy of Sciences of Belarus, Belarusian State University, Anti-Doping Laboratory

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Belarusian Republican Foundation for Fundamental Research, Ministry of Education of the Republic of Belarus

Awards: G3761264232, G5978275110