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 50 条
  • [41] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions
    Beletskaya, Irina P.
    Cheprakov, Andrei V.
    ORGANOMETALLICS, 2012, 31 (22) : 7753 - 7808
  • [42] Rapid and Highly Efficient Microwave-Assisted C-N, C-O and C-S Coupling Reactions without a Transition-Metal Catalyst
    Yuan, Yanqin
    Guo, Shengrong
    Mo, Jianjun
    Qian, Li
    Shi, Zefeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (04) : 732 - 741
  • [43] Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions
    Jarvo, Elizabeth R.
    Sanford, Amberly B.
    SYNLETT, 2021, 32 (12) : 1151 - 1156
  • [44] Practical heterogeneous photoredox/nickel dual catalysis for C-N and C-O coupling reactions
    Liu, Yi-Yin
    Liang, Dong
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    CHEMICAL COMMUNICATIONS, 2019, 55 (33) : 4853 - 4856
  • [45] Palladium supported on zinc ferrite: an efficient catalyst for ligand free C-C and C-O cross coupling reactions
    Singh, Abhilash S.
    Shendage, Suresh S.
    Nagarkar, Jayashree M.
    TETRAHEDRON LETTERS, 2013, 54 (47) : 6319 - 6323
  • [46] A facile route to functionalized naphthalimide dyes via copper-catalyzed C-N, C-O, and C-S cross-coupling reactions in aqueous medium
    Bardajee, Ghasem Rezanejade
    TETRAHEDRON LETTERS, 2013, 54 (36) : 4937 - 4941
  • [47] Chitosan@Cu2O as A Facile, Efficient and Reusable Catalyst for Ligand-Free C-O and C-N Coupling
    Qian, Cunwei
    Zhu, Wenqian
    Liu, Junlong
    Wang, Xuemin
    Qiu, Ligan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (06) : 1695 - 1703
  • [48] External electric field, a potential catalyst for C-N cross-coupling reaction
    Yadav, Priyanka
    Kumar, Pradeep
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2023, 25 (48) : 32807 - 32812
  • [49] Beyond C-H and C-O activation: the evolution of components in cross-coupling reactions
    Chen, Kang
    Zhang, Xi-Sha
    Shi, Zhang-Jie
    PURE AND APPLIED CHEMISTRY, 2014, 86 (03) : 361 - 372
  • [50] Insight into C-C and C-N cross-coupling reactions involving nickel NHC derivatives
    Baldwin, Steven M.
    Del Ciello, Sarah A.
    Witzke, Ryan J.
    Hillhouse, Gregory L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247