Work

Direct catalyst-free photochemical C(sp3)–H bond functionalization of cyclic ethers with Michael acceptors

Year: 2025

Type: article

Abstract: Photochemical functionalization of C(sp 3 )-H bonds provides an important tool in the arsenal of organic chemists to promote valuable transformations. Exploring the capabilities and limitations of light-driven reactions, in this study, we present a catalyst-free protocol for the activation of the α -C-H bond of five-membered cyclic ethers by employing 390 nm LED irradiation. A variety of Michael acceptors participated in the reaction, leading to the desired products in moderate to high yields. Mechanistic studies, through High Resolution Mass Spectrometry (HRMS) and on/off experiments, proved the necessity of light for the reaction to occur, while also providing a plausible reaction mechanism.

Source: Tetrahedron

DOI: 10.1016/j.tet.2025.134834

Authors: Manos V.G. Lantzanakis, Naya A. Stini, Christoforos G. Kokotos

Institution: National and Kapodistrian University of Athens

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,680

Funder: Hellenic Foundation for Research and Innovation