2-(2,6-Dimethylphenylamino)-2-oxoacetic Acid as an Efficient Prompter for the Copper-Catalyzed Hydroxylation of Aryl Bromides

被引：2
|
作者：
Liu, Xiangqian [1 ]
Zhang, Hui [1 ]
Jiang, Yongwen [2 ]
机构：
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 32卷 / 08期
基金：
中国国家自然科学基金;
关键词：
copper; Ullmann reaction; 2-(2,6-dimethylphenylamino)-2-oxoacetic acid; hydroxylation; phenol; SUBSTITUTED PHENOLS; HALIDES; ARYLATION;
D O I：
10.6023/cjoc201206001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
CuI/2-(2,6-dimethylphenylamino)-2-oxoacetic acid (DMPAO) as an efficient catalytic combination was used for the hydroxylation of aryl bromides. The catalyst loading is low to 2 mol% and substituted phenols could be prepared in wide assembly. In addition, by modifying the mixed solvent and base the symmetrical diaryl ethers could be synthesized conveniently from aryl bromides.
引用
收藏
页码：1434 / 1438
页数：5
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  • [4] Electrochemical hydroxylation of organoboron compounds
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    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (19) : 5853 - 5858
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