Litcius/Paper detail

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

Petros L. Gkizis, Constantinos T. Constantinou, Christoforos G. Kokotos

2023European Journal of Organic Chemistry13 citationsDOIOpen Access PDF

Abstract

Abstract 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.

Topics & Concepts

ChemistryBoronic acidMoietyCatalysisPhotoredox catalysisPhenolFunctional groupCombinatorial chemistryOrganic chemistryPhotocatalysisPhotochemistryPolymerRadical Photochemical ReactionsAdvanced Photocatalysis TechniquesCatalytic Cross-Coupling Reactions