Copper-Catalyzed Dehydrogenative Coupling of Arenes with Alcohols

被引：83
作者：
Bhadra, Sukalyan [1 ]
Matheis, Christian [1 ]
Katayev, Dmitry [1 ]
Goossen, Lukas J. [1 ]
机构：
[1] Tech Univ Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 35期
关键词：
CH activation; CO coupling; copper; dehydrogenative cross-coupling; homogeneous catalysis; C-H BOND; FREE SILVER(I) ALKOXIDE; ORTHO-ARYLATION; OXIDATIVE FUNCTIONALIZATION; INTERMOLECULAR DEHYDRATION; SODIUM PERSULFATE; SINGLE-ELECTRON; DIRECTING GROUP; ARYL ETHERS; ACTIVATION;
D O I：
10.1002/anie.201303702
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
What a couple! Arenes functionalized with donating groups undergo oxidative dehydrogenative coupling with alcohols in the presence of a copper/silver catalyst system. This intermolecular C-H alkoxylation provides a convenient synthetic route to the important class of aryl ethers. The catalyst system also allows the alkoxylation of benzylic C-H groups with formation of benzyl alkyl ethers. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9279 / 9283
页数：5
相关论文
共 106 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]  
[Anonymous], 2013, Angew. Chem
[4]  
Bhadra S., 2013, ANGEW CHEM, V125, P3031
[5]   Synthesis of Aryl Ethers from Benzoates through Carboxylate-Directed C-H-Activating Alkoxylation with Concomitant Protodecarboxylation [J].
Bhadra, Sukalyan ;
Dzik, Wojciech I. ;
Goossen, Lukas J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) :2959-2962
[6]   Decarboxylative Etherification of Aromatic Carboxylic Acids [J].
Bhadra, Sukalyan ;
Dzik, Wojciech I. ;
Goossen, Lukas J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) :9938-9941
[7]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[8]   Pd-Catalyzed Dehydrogenative Cross-Coupling of Polyfluoroarenes with Heteroatom-Substituted Enones [J].
Chen, Fei ;
Feng, Zhang ;
He, Chun-Yang ;
Wang, Hao-Yang ;
Guo, Yin-long ;
Zhang, Xingang .
ORGANIC LETTERS, 2012, 14 (04) :1176-1179
[9]   Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].
Chen, Long ;
Shi, Erbo ;
Liu, Zhaojun ;
Chen, Shulin ;
Wei, Wei ;
Li, Hong ;
Xu, Kai ;
Wan, Xiaobing .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089
[10]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
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