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

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

1, 1 and 1,2,* email
Received: 25 June 2012; in revised form: 6 July 2012 / Accepted: 12 July 2012 / Published: 18 July 2012
(This article belongs to the Special Issue Hypervalent Compounds)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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®
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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.

AMA Style

Uyanik M, Mutsuga T, Ishihara K. IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®. Molecules. 2012; 17(7):8604-8616.

Chicago/Turabian Style

Uyanik, Muhammet; Mutsuga, Tatsuya; Ishihara, Kazuaki. 2012. "IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®." Molecules 17, no. 7: 8604-8616.


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