Aerobic Organocatalytic Oxidation of Aryl Aldehydes: Flavin Catalyst Turnover by Hantzsch's Ester

Shuai Chen and Frank W. Foss, Jr*

*The University of Texas at Arlington, Department of Chemistry and Biochemistry, Arlington, Texas 76019-0065, United States, Email: ffossuta.edu

S. Chen, F. W. Foss, Jr, Org. Lett., 2012, 14, 5150-5153.

DOI: 10.1021/ol302479b

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Abstract

The use of flavin organocatalysts and a Hantzsch ester enabled a transition-metal-free Dakin oxidation fueled by molecular oxygen as the terminal oxidant. Catechols and electron-rich phenols are achieved with low catalyst loadings, in the presence of Hantzsch ester, and O₂ or air as the stoichiometric oxidant source.

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Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

S. Chen, M. S. Hoassain, F. W. Foss, Jr, Org. Lett., 2012, 14, 2806-2809.

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Key Words

Dakin Reaction, Organocatalysis, Oxygen

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ID: J54-Y2012-3270