Benzoquinone-Promoted Aerobic Oxidative Hydroxylation of Arylboronic Acids in Water

Guolin Cheng; Xiaobao Zeng; Xiuling Cui

doi:10.1055/s-0033-1338571

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(03): 295-300
DOI: 10.1055/s-0033-1338571

paper

Benzoquinone-Promoted Aerobic Oxidative Hydroxylation of Arylboronic Acids in Water

Guolin Cheng

Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institute of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. of China eMail: cuixl@hqu.edu.cn

,

Xiaobao Zeng

Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institute of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. of China eMail: cuixl@hqu.edu.cn

,

Xiuling Cui*

Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institute of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. of China eMail: cuixl@hqu.edu.cn

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Abstract

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Abstract

A general and efficient aerobic oxidative hydroxylation of arylboronic acids promoted by benzoquinone in water was realized, and provided phenols in 72–95% yields for 20 examples. The main advantages of this protocol are the use of water as solvent in the presence of a catalytic amount of benzoquinone, and metal-free conditions.

Key words

benzoquinone - arylboronic acids - oxidation - oxygen - phenols

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