UVA‐Light‐Promoted Catalyst‐Free Photochemical Aerobic Oxidation of Boronic Acids

The hydroxy group, and the phenol moiety in particular, is ubiquitous in several natural products, in organic synthesis and/or pharmaceutical industry. With the uprise of photoredox catalysis, many efforts worldwide focus on developing novel and sustainable protocols, providing an easy access to hyd...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-11, Vol.26 (44), p.n/a
Main Authors: Gkizis, Petros L., Constantinou, Constantinos T., Kokotos, Christoforos G.
Format: Article
Language:English
Subjects:
aerobic oxidation
boronic acids
Catalysis
catalyst-free
Irradiation
Natural products
Oxidation
phenols
photochemistry
Photooxidation
Photoredox catalysis
Reaction mechanisms
Substrates
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Summary:The hydroxy group, and the phenol moiety in particular, is ubiquitous in several natural products, in organic synthesis and/or pharmaceutical industry. With the uprise of photoredox catalysis, many efforts worldwide focus on developing novel and sustainable protocols, providing an easy access to hydroxy‐containing molecules. Boronic acids and boronic ester derivatives are considered valuable precursors for the synthesis of hydroxy group derivatives. Herein, we report a novel, sustainable, light‐driven protocol, where the impact of wavelength irradiation on boronic acid aerobic photooxidation was examined. In this work, UVA‐light (370 nm) irradiation was found to promote the photocatalyst‐free aerobic oxidation of boronic acids and boronic acid derivatives. Furthermore, a broad scope of substrates was tested, and extensive mechanistic studies were performed in order to probe the reaction mechanism. Tuning the irradiation source wavelength provides the advantage in developing a catalyst‐free photooxidative protocol based on boronic acid‐ DIPEA complex's ability to generate reactive oxygen species.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300898