An in situ generated CuI/metformin complex as a novel and efficient catalyst for C-N and C-O cross-coupling reactions

被引:40
作者
Ghorbani-Vaghei, Ramin [1 ]
Hemmati, Saba [1 ]
Veisi, Hojat [2 ]
机构
[1] Bu Ali Sina Univ, Dept Organ Chem, Fac Chem, Hamadan, Iran
[2] PNU, Dept Chem, Tehran 193954697, Iran
关键词
CuI; Ullmann condensation; Biguanide; Catalysis; Coupling reactions; ARYL HALIDES; HIGHLY EFFICIENT; COPPER; ARYLATION; IMIDAZOLES; PHENOLS; MILD; INHIBITORS; BROMIDES; LIGAND;
D O I
10.1016/j.tetlet.2013.10.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An in situ generated complex of copper(I) and a biguanide, namely metformin, was found to be a highly efficient homogeneous catalyst in N/O-arylation reactions. The O-arylation of substituted phenols with various aryl iodides and bromides was also achieved using this copper catalyst to afford diaryl ethers in good to excellent yields in DMF. This heterogeneous copper catalyst also promotes the N-arylation of imidazole with a variety of aryl halides (Cl, Br, I) in acetonitrile. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:7095 / 7099
页数:5
相关论文
共 68 条
[1]   Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions [J].
Alcalde, E ;
Dinarès, I ;
Rodríguez, S ;
de Miguel, CG .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1637-1643
[2]   Highly efficient phosphine-free Suzuki aryl couplings mediated by an in situ generated Pd(OAc)2/metformin complex in green media [J].
Alizadeh, A. ;
Khodaei, M. M. ;
Kordestani, D. ;
Beygzadeh, M. .
TETRAHEDRON LETTERS, 2013, 54 (04) :291-294
[3]   The successful synthesis of biguanide-functionalized mesoporous silica catalysts: Excellent reactivity combined with facile catalyst recyclability [J].
Alizadeh, A. ;
Khodaei, M. M. ;
Kordestani, D. ;
Fallah, A. H. ;
Beygzadeh, M. .
MICROPOROUS AND MESOPOROUS MATERIALS, 2012, 159 :9-16
[4]  
[Anonymous], 2012, INVEST OPHTH VIS SCI, V53, P53
[5]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[6]   SYNTHESIS OF N-EPSILON-(P-BROMOPHENYL)-L-LYSINE AND N-TAU-(P-BROMOPHENYL)-L-HISTIDINE AS MODELS FOR ADDUCTS OF BROMOBENZENE 3,4-OXIDE TO PROTEIN - OBSERVATION OF AN UNUSUAL PD-CATALYZED N-TAU-ARYL TO N-PI-ARYL SUBSTITUENT MIGRATION [J].
BAMBAL, R ;
HANZLIK, RP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :729-732
[7]   Ligand-free solid supported palladium(0) nano/microparticles promoted C-O, C-S, and C-N cross coupling reaction [J].
Bandna ;
Guha, Nitul Ranjan ;
Shil, Arun K. ;
Sharma, Dharminder ;
Das, Pralay .
TETRAHEDRON LETTERS, 2012, 53 (39) :5318-5322
[8]   Copper-catalyzed synthesis of vinyl sulfides [J].
Bates, CG ;
Saejueng, P ;
Doherty, MQ ;
Venkataraman, D .
ORGANIC LETTERS, 2004, 6 (26) :5005-5008
[9]   Copper-catalyzed synthesis of 1,3-enynes [J].
Bates, CG ;
Saejueng, P ;
Venkataraman, D .
ORGANIC LETTERS, 2004, 6 (09) :1441-1444
[10]   Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione [J].
Buck, E ;
Song, ZJ ;
Tschaen, D ;
Dormer, PG ;
Volante, RP ;
Reider, PJ .
ORGANIC LETTERS, 2002, 4 (09) :1623-1626