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使用叔丁基过氧化氢和水通过碘引发的芳基烯烃双氧化反应:一种合成邻二醇和双过氧化物的方法。

Iodine-Initiated Dioxygenation of Aryl Alkenes Using -Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides.

作者信息

Gao Xiaofang, Lin Jiani, Zhang Li, Lou Xinyao, Guo Guanghui, Peng Na, Xu Huan, Liu Yi

机构信息

Key Laboratory of Coal Conversion and New Carbon Materials of Hubei Province, College of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan 430081, P. R. China.

State Key Laboratory of Membrane of Separation and Membrane Process, School of Chemistry and Chemical Engineering & School of Environmental Science and Engineering, Tiangong University, Tianjin 300378, P. R. China.

出版信息

J Org Chem. 2021 Nov 5;86(21):15469-15480. doi: 10.1021/acs.joc.1c01968. Epub 2021 Oct 27.

Abstract

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and -butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, NaCO as the additive, and propylene carbonate as the solvent, instead.

摘要

已开发出一种在水中以碘为催化剂、叔丁基过氧化氢(TBHPs)为氧化剂,用于构建邻二醇的环境友好且高效的芳基烯烃双氧化反应。该方法高效、可持续且操作简单。详细的机理研究表明,其中一个羟基来源于水,另一个来源于叔丁基过氧化氢。此外,以碘为催化剂、碳酸钠为添加剂、碳酸丙烯酯为溶剂时,可相反地以良好产率获得双过氧化物。

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