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CsOH catalyzed aerobic oxidative synthesis of p-quinols from multi-alkyl phenols under mild conditions

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Abstract

p-Quinols are ubiquitous structural motifs of various natural products and pharmaceutical compounds, and versatile building blocks in synthetic chemistry. The reported methods for the synthesis of p-quinol require stoichiometric amounts of oxidants. Molecular oxygen is considered as an ideal oxidant due to its natural, inexpensive, and environmentally friendly characteristics. During the ongoing research of C-H bond hydroxylation, we found that multi-alkyl phenols could react with molecular oxygen under mild conditions. Herein, we describe an efficient oxidative de-aromatization of multi-alkyl phenols to p-quinols. 1 atm of molecular oxygen was used as the oxidant. Many multi-alkyl phenols could react smoothly at room temperature. Isotopic labeling experiment was also performed, and the result proved that the oxygen atom in the produced hydroxyl group is from molecular oxygen.

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Authors and Affiliations

  1. State Key Laboratory of Natural and Biomimetic Drugs; School of Pharmaceutical Sciences, Peking University, Beijing, 100191, China

    Yu-Feng Liang, Kai Wu, Xiaoyang Wang, Yujie Liang & Ning Jiao

  2. The Key Laboratory of Oil and Gas Fine Chemicals; Ministry of Education & Xinjiang Uygur Autonomous Region, Xinjiang University, Urumqi, 830046, China

    Zhiqing Liu & Chenjiang Liu

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  1. Yu-Feng Liang
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  2. Kai Wu
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  3. Zhiqing Liu
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  4. Xiaoyang Wang
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  5. Yujie Liang
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Correspondence to Chenjiang Liu or Ning Jiao.

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Liang, YF., Wu, K., Liu, Z. et al. CsOH catalyzed aerobic oxidative synthesis of p-quinols from multi-alkyl phenols under mild conditions. Sci. China Chem. 58, 1334–1339 (2015). https://doi.org/10.1007/s11426-015-5363-4

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