Anthraquinone-Catalyzed Photooxidation of Boronic Acids in a Bio-Based Solvent (2-Me-THF)

In memory of Emeritus Professor Demetrios N. Nicolaides (Aristotle University of Thessaloniki), who passed away in December 2022.

Abstract

The phenol moiety appears in a wide variety of natural products, exhibiting biological activity, and in numerous active pharmaceutical compounds. Boronic acids are potential precursors of the phenol scaffold, and a plethora of efforts has been focused in developing novel and green protocols, targeting their chemoselective transformation into phenols. Photochemistry is a rapidly expanding research field converting light energy into chemical potential. Photochemical aerobic processes possess additional advantages to photochemistry and may find applications in chemical industries. Herein, a low-catalyst-loading anthraquinone-catalyzed photochemical process is demonstrated, under CFL lamp irradiation, while exploiting 2-Me-THF as the reaction medium for the conversion of boronic acids into phenols. Furthermore, a broad substrate scope was employed.

Key words

photochemistry - aerobic oxidation - green chemistry - boronic acid - anthraquinone

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