Copper-Catalyzed Regioselective C-H Aerobic Oxidative Cycloetherification of o-Arylphenols Bearing an Additional Directing Group

被引:15
作者
Zhao, Jiaji [1 ,2 ]
Wang, Yong [1 ,2 ]
Zhu, Qiang [1 ,2 ]
机构
[1] Chinese Acad Sci, Guangzhou Inst Biomed, State Key Lab Resp Dis, 190 Kaiyuan Ave, Guangzhou 510530, Guangdong, Peoples R China
[2] Chinese Acad Sci, Guangzhou Inst Hlth, State Key Lab Resp Dis, Guangzhou 510530, Guangdong, Peoples R China
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 10期
基金
美国国家科学基金会;
关键词
chelation; copper catalysis; cycloetherification; dibenzofuran; oxidative annulation; N BOND FORMATION; DIRECT ARYLATION; DIBENZOFURANS; FUNCTIONALIZATION; CYCLIZATION; CARBAZOLES; IODOANILINES; IODOPHENOLS; ACTIVATION; ATMOSPHERE;
D O I
10.1055/s-0031-1290966
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed C-H oxidative cycloetherification of o-arylphenols containing an additional directing group under an oxygen atmosphere was developed. 2,6-Disubstituted dibenzofuran derivatives were prepared by regioselective activation of the sterically more hindered C-H bond. The presence of the extra directing group not only controls the regioselectivity, but also increases the cyclization efficiency significantly.
引用
收藏
页码:1551 / 1555
页数:5
相关论文
共 30 条
[1]   Ligand-free copper(I)-catalysed intramolecular direct C-H functionalization of azoles [J].
Barbero, Nekane ;
SanMartin, Raul ;
Dominguez, Esther .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) :841-845
[2]   Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].
Bernini, Roberta ;
Fabrizi, Giancarlo ;
Sferrazza, Alessio ;
Cacchi, Sandro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081
[3]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[4]   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
[5]   Achyrofuran, a new antihyperglycemic dibenzofuran from the South American medicinal plant Achyrocline satureioides [J].
Carney, JR ;
Krenisky, JM ;
Williamson, RT ;
Luo, J .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (02) :203-205
[6]   Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation [J].
Chen, Bo ;
Hou, Xue-Long ;
Li, Yu-Xue ;
Wu, Yun-Dong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7668-7671
[7]   Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].
Cho, Seung Hwan ;
Yoon, Jungho ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005
[8]   Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action [J].
De Lombaert, S ;
Blanchard, L ;
Stamford, LB ;
Tan, J ;
Wallace, EM ;
Satoh, Y ;
Fitt, J ;
Hoyer, D ;
Simonsbergen, D ;
Moliterni, J ;
Marcopoulos, N ;
Savage, P ;
Chou, M ;
Trapani, AJ ;
Jeng, AY .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :488-504
[9]   Cu(II) Catalyzed Imine C-H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles [J].
Guin, Srimanta ;
Ghosh, Tuhin ;
Rout, Saroj Kumar ;
Banerjee, Arghya ;
Patel, Bhisma K. .
ORGANIC LETTERS, 2011, 13 (22) :5976-5979
[10]   Observation and Mechanistic Study of Facile C-O Bond Formation between a Well-Defined Aryl-Copper(III) Complex and Oxygen Nucleophiles [J].
Huffman, Lauren M. ;
Casitas, Alicia ;
Font, Marc ;
Canta, Merce ;
Costas, Miquel ;
Ribas, Xavi ;
Stahl, Shannon S. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (38) :10643-10650