Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions

被引：16

作者：

Mou, Fen ^{[1
]}

Sun, Yadong ^{[1
]}

Jin, Weiwei ^{[1
]}

Zhang, Yonghong ^{[1
]}

Wang, Bin ^{[1
]}

Liu, Zhiqing ^{[1
]}

Guo, Lei ^{[1
]}

Huang, Jianbin ^{[1
]}

Liu, Chenjiang ^{[1
]}

机构：

[1] Xinjiang Univ, Key Lab Oil & Gas Fine Chem, Urumqi Key Lab Green Catalysis & Synth Technol, Minist Educ,Sch Chem & Chem Engn,Phys & Chem Dete, Xinjiang Uygur Autonomou 830046, Urumqi, Peoples R China

来源：

RSC ADVANCES | 2017年 / 7卷 / 37期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; HIGHLY EFFICIENT; IN-SITU; ESTERS; FUNCTIONALIZATION; ANNULATION; LACTONES;

D O I：

10.1039/c7ra02788e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free protocol for the direct oxidative esterification of the Csp(3)-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.

引用

页码：23041 / 23045

页数：5

共 43 条

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[17] Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3-H bond activation using a new metal-organic framework as catalyst
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Le, Ha V.
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[20] Metal-free activation of H2O2 by synergic effect of ionic liquid and microwave: chemoselective oxidation of benzylic alcohols to carbonyls and unexpected formation of anthraquinone in aqueous condition
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