Copper-Catalyzed Etherification of Arene C-H Bonds

被引:180
作者
Roane, James [1 ]
Daugulis, Olafs [1 ]
机构
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
关键词
CARBON-CARBON BONDS; COUPLING REACTIONS; C(SP(2))-H BONDS; PALLADIUM; ARYLATION; C(SP(3))-H; HYDROGEN; FUNCTIONALIZATIONS; OXYGENATIONS; ALKOXYLATION;
D O I
10.1021/ol402904d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for direct, auxiliary-assisted alkoxylation and phenoxylation of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of amine derivatives is reported. The reaction employs (CuOH)(2)CO3 catalyst, air as an oxidant, phenol or alcohol coupling partner, DMF, pyridine, or DMPU solvent, and K2CO3, tetramethylguanidine, or K3PO4 base at 70-130 degrees C.
引用
收藏
页码:5842 / 5845
页数:4
相关论文
共 50 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]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[5]   Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986
[6]   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
[7]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[8]   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
[9]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[10]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655