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

被引：62

作者：

Uyanik, Muhammet ^{[1
]}

Mutsuga, Tatsuya ^{[1
]}

Ishihara, Kazuaki ^{[1
,2
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Nagoya Univ, CREST, Japan Sci & Technol Agcy JST, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

MOLECULES | 2012年 / 17卷 / 07期

关键词：

oxidation; phenol; o-quinone; 2-iodoxybenzenesulfonic acid (IBS); Oxone (R); HYPERVALENT IODINE OXIDATION; 4-IODOPHENOXYACETIC ACID; P-QUINONES; 2-IODOXYBENZENESULFONIC ACID; SELECTIVE OXIDATION; DERIVATIVES; DEAROMATIZATION; BENZOQUINONES; ALKOXYPHENOLS; CHEMISTRY;

D O I：

10.3390/molecules17078604

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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(R) 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 (nBu(4)NHSO(4)), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).

引用

页码：8604 / 8616

页数：13

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