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
  • [11] FUNGICIDAL ACTIVITY AND CHEMICAL CONSTITUTION .11. ACTIVITY OF N-ALKYL GUANIDINE ACETATES
    BYRDE, RJW
    WOODCOCK, D
    CLIFFORD, DR
    [J]. ANNALS OF APPLIED BIOLOGY, 1962, 50 (02) : 291 - &
  • [12] Preparation of N-aryl compounds by amino acid-promoted Ullmann-type coupling reactions
    Cai, Q
    Zhu, W
    Zhang, H
    Zhang, YD
    Ma, DW
    [J]. SYNTHESIS-STUTTGART, 2005, (03): : 496 - 499
  • [13] Simple and efficient CuI/PEG-400 system for amination of aryl halides with aqueous ammonia
    Chen, Junmin
    Yuan, Tangjun
    Hao, Wenyan
    Cai, Mingzhong
    [J]. TETRAHEDRON LETTERS, 2011, 52 (29) : 3710 - 3713
  • [14] Thermally decomposed Cu-Fe-hydrotalcite. A novel highly active catalyst for o-arylation of naphthol and phenols by aryl halides
    Choudhary, V. R.
    Dumbre, D. K.
    Yadav, P. N.
    Bhargava, S. K.
    [J]. CATALYSIS COMMUNICATIONS, 2012, 29 : 132 - 136
  • [15] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides
    Cristau, HJ
    Cellier, PP
    Spindler, JF
    Taillefer, M
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) : 5607 - 5622
  • [16] SYNTHETIC ANTIMALARIALS .28. AN ALTERNATIVE ROUTE TO N-1-ARYL-N-5-ALKYLDIGUANIDES
    CURD, FHS
    HENDRY, JA
    KENNY, TS
    MURRAY, AG
    ROSE, FL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1948, (OCT): : 1630 - 1636
  • [17] Amino acid-mediated Goldberg reactions between amides and aryl iodides
    Deng, W
    Wang, YF
    Zou, W
    Liu, L
    Guo, QX
    [J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2311 - 2315
  • [18] Mild and regioselective bromination of aromatic compounds with N,N,N′,N′-tetrabromobenzene-1,3-disulfonylamide an poly (N-bromobenzene-1,3-di-sulfonylamide)
    Ghorbani-Vaghei, R
    Jalili, H
    [J]. SYNTHESIS-STUTTGART, 2005, (07): : 1099 - 1102
  • [19] Poly(N,N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-Tetrachlorobenzene-1,3-disulfonamide as Novel Reagents for the Synthesis of N-Chloroamines, Nitriles and Aldehydes
    Ghorbani-Vaghei, Ramin
    Veisi, Hojat
    [J]. SYNTHESIS-STUTTGART, 2009, (06): : 945 - 950
  • [20] Hadden DR, 2005, J ROY COLL PHYS EDIN, V35, P258