Copper-Mediated Direct Aryloxylation of Benzamides Assisted by an N,O-Bidentate Directing Group

被引:104
作者
Hao, Xin-Qi [1 ]
Chen, Li-Juan [1 ]
Ren, Baozeng [2 ]
Li, Liu-Yan [1 ]
Yang, Xin-Yan [1 ]
Gong, Jun-Fang [1 ]
Niu, Jun-Long [1 ]
Song, Mao-Ping [1 ]
机构
[1] Zhengzhou Univ, Henan Key Lab Chem Biol & Organ Chem, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Sch Chem Engn & Energy, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; BIDENTATE-CHELATION ASSISTANCE; CROSS-COUPLING REACTIONS; DIARYL ETHERS; AROMATIC AMIDES; DIRECT ARYLATION; ACID DERIVATIVES; ACTIVATION; ARYL; FUNCTIONALIZATION;
D O I
10.1021/ol500166d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-mediated selective mono- or diaryloxylation of benzamides has been achieved by using 2-aminopyridine 1-oxide as a new and removable N,O-bidentate directing group. The reaction system shows a broad substrate scope and provides a straightforward way for the synthesis of mono- and diaryloxylated benzoic acids.
引用
收藏
页码:1104 / 1107
页数:4
相关论文
共 63 条
[1]   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
[2]   Ruthenium-catalyzed direct arylation of C-H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation [J].
Aihara, Yoshinori ;
Chatani, Naoto .
CHEMICAL SCIENCE, 2013, 4 (02) :664-670
[3]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[4]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[5]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[6]  
Bhadra S., 2013, ANGEW CHEM INT EDIT, V52, P1
[7]   Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].
Bistri, Olivia ;
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588
[8]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[9]   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
[10]   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