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

Authors :
Gkizis, Petros L.
Serviou, Stamatis K.
Balaskas, Angelos
Constantinou, Constantinos T.
Triandafillidi, Ierasia
Kokotos, Christoforos G.
Source :
Synlett. Feb2024, Vol. 35 Issue 3, p330-336. 7p.
Publication Year :
2024

Abstract

This article discusses the use of boronic acids in the synthesis of phenols, which are important compounds found in natural products and pharmaceuticals. The researchers focus on developing environmentally friendly and sustainable methods for preparing phenols from boronic acids. They explore different photocatalysts and solvents to optimize the oxidation reaction. The study finds that anthraquinone is an effective photocatalyst and 2-Me-THF is the best solvent for the reaction. The researchers aim to provide a more sustainable protocol for the oxidation of boronic acids. Another study described in the document investigates the photochemical aerobic oxidation of boronic acids to phenols. The researchers tested different additives and found that N,N'-diisopropylethylamine (DIPEA) was the most suitable base, resulting in the complete formation of phenol. They also explored the range of substrates and found that various aryl-substituted boronic acids could be converted into the corresponding phenols with moderate to excellent yields. Mechanistic studies suggested a mixed pathway involving the generation of a superoxide anion and the formation of hydrogen peroxide. Overall, this study presents an environmentally friendly and efficient method for the oxidation of boronic acids. [Extracted from the article]

Details

Language :
English
ISSN :
09365214
Volume :
35
Issue :
3
Database :
Academic Search Index
Journal :
Synlett
Publication Type :
Academic Journal
Accession number :
175119271
Full Text :
https://doi.org/10.1055/a-2071-7077