Work

Anticipating Natural Phenolics Through Visible Light‐Induced Photorearrangement of Quinones

Year: 2025

Type: article

Abstract: A general protocol for the photorearrangement of substituted benzo‐ and naphthoquinones using monochromatic blue light irradiation in solution was developed. During this process, the quinone ring is transformed into the hydroquinone, while the substituent undergoes desaturation or annulation onto the proximal oxygen of the formed hydroquinone. We found that desaturation was preferred for acyclic saturated substituents, such as alkyl groups, and the tendency for annulation was observed for both cyclic and acyclic unsaturated substituents (allyl, alkenyl, aryl). The diversity of the participating substituents and the functional group tolerance of this transformation allowed us to prepare 10 natural phenolic compounds, suggesting that visible light may likewise induce their formation from the respective quinones in natural sources.

Source: ChemistryEurope

DOI: 10.1002/ceur.202400094

Authors: Alexander A. Fadeev, Martin Kotora

Institution: Charles University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Univerzita Karlova v Praze, Grantová Agentura České Republiky

Awards: Catalytic Cyclotrimerization and C-C/C-H Functionalization Reactions in the Synthesis of Functional Molecules, G979189628