Oxidation of 4-arylphenol trimethylsilyl ethers to p-arylquinols using hypervalent iodine(III) reagents
Oxidation of 4-arylphenol trimethylsilyl ethers to p-arylquinols using hypervalent iodine(III) reagents
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DOI：
10.1016/j.tetlet.2006.11.073
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发表时间：
2007-01-15
影响因子：
1.8
通讯作者：
Felpin, Francois-Xavier
中科院分区：
文献类型：
--
作者：
Felpin, Francois-Xavier
报道了4-芳基酚三甲基硅醚与苯碘啶（III）二乙酸酯（PIDA）氧化合成对芳基喹啉的高效方法。与用高价碘（III）试剂氧化游离苯酚相比，该方案通过最小化低聚物副产物大大提高了对喹啉的收率。苯基吡啶（III）二乙酸酯的无害性与温和的条件相结合，使该方法在金属介导的氧化反应中具有很强的竞争力。讨论了所提出的反应机理，并与普遍接受的4-取代酚的反应机理进行了比较，以解释收率的提高。(c) 2006 Elsevier Ltd.版权所有。
An efficient synthesis of p-arylquinols by the oxidation of 4-arylphenol trimethylsilyl ethers with phenyliodine(III) diacetate (PIDA) is reported. This protocol greatly improved the yield of p-quinol by minimizing oligomer side products compared to the oxidation of free phenol with hypervalent iodine(III) reagents. The innocuity of phenyliodine(III) diacetate associated with the mild conditions make the method highly competitive over metal-mediated oxidation reactions. The proposed reaction mechanism is discussed and compared to the generally accepted mechanism of 4-substituted phenols to explain the yield improvement. (c) 2006 Elsevier Ltd. All rights reserved.