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Molecules 2012, 17(7), 8604-8616; doi:10.3390/molecules17078604

IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

1
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan
2
Japan Science and Technology Agency (JST), CREST, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan
*
Author to whom correspondence should be addressed.
Received: 25 June 2012 / Revised: 6 July 2012 / Accepted: 12 July 2012 / Published: 18 July 2012
(This article belongs to the Special Issue Hypervalent Compounds)
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Abstract

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone® as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).
Keywords: xidation; phenol; o-quinone; 2-iodoxybenzenesulfonic acid (IBS); Oxone® xidation; phenol; o-quinone; 2-iodoxybenzenesulfonic acid (IBS); Oxone®
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MDPI and ACS Style

Uyanik, M.; Mutsuga, T.; Ishihara, K. IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®. Molecules 2012, 17, 8604-8616.

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