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).
Highlights
Introduction oQuinones are useful synthetic intermediates for the synthesis of medicinally and biologically important compounds [1,2,3,4,5,6,7,8,9,10,11]
In 2010, Harvey and colleagues reported the regiospecific oxidation of polycyclic aromatic phenols to quinones using hypervalent iodine(III and V)
As part of our continuing interest in the IBS-catalyzed oxidation system, we report here the in situ-generated IBS-catalyzed regioselective oxidation of phenols to o-quinones with Oxone®
Summary
Quinones are useful synthetic intermediates for the synthesis of medicinally and biologically important compounds [1,2,3,4,5,6,7,8,9,10,11]. Numerous methods have been reported for the preparation of p-quinones by the oxidation of phenols or their derivatives [12,13,14]. After Pettus’ pioneering findings, this method was applied to the synthesis of biologically active compounds such as catecholestrogen [20], catecholamine [21], hydroxytyrosol [22], and flavonoid [23] derivatives. In 2010, Harvey and colleagues reported the regiospecific oxidation of polycyclic aromatic phenols to quinones using hypervalent iodine(III and V)
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