A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water

被引:21
|
作者
Kodicherla, Balaswamy [1 ]
Perumgani, Pullaiah C. [1 ]
Mandapati, Mohan Rao [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, I & PC Div, Hyderabad 500607, Andhra Pradesh, India
关键词
Polystyrene-supported Cu(II) catalyst; N-arylation; Sonogashira cross-coupling; Aryl halide; Aqueous solution; RECYCLABLE CATALYST; HIGHLY EFFICIENT; PALLADIUM-FREE; ARYL HALIDES; C-N; COMPLEX; ULLMANN; ALKYNES; SUZUKI; ACETYLENES;
D O I
10.1016/j.apcata.2014.07.001
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A polymer-anchored Cu(II) N,N-dimethylethylenediamine complex was prepared and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), atomic absorption spectroscopy (AAS), and thermogravimetric analysis (TGA). This heterogeneous Cu(II) catalyst, efficiently works for the N-arylation of indoles and Sonogashira coupling of terminal alkynes with aryl halides in aqueous medium. The effect of solvent, and base for the C-N, and C-C coupling reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to four times without significant loss of its catalytic activity. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:110 / 115
页数:6
相关论文
共 50 条
  • [1] Highly efficient and reusable polystyrene-supported copper(II) catalytic system for S-arylation of potassium thiocyanate by aryl halides in water
    Hajipour, Abdol R.
    Jajarmi, Saeideh
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (07) : 566 - 570
  • [2] Advances on N-Arylation of Indoles by Cross-Coupling Reactions
    Xu, Hui
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2009, 6 (04) : 367 - 377
  • [3] Copper(II)-mediated regioselective N-arylation of pyrroles, indoles, pyrazoles and carbazole via dehydrogenative coupling
    Sadhu, Pradeep
    Punniyamurthy, Tharmalingam
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (13) : 2803 - 2806
  • [4] A green, homogeneous and reusable surfactant/copper based ionic liquid for the N-arylation of indoles, pyrazoles and imidazoles
    Heidarizadeh, Fariba
    Majdi-nasab, Afrooz
    [J]. TETRAHEDRON LETTERS, 2015, 56 (46) : 6360 - 6363
  • [5] EFFICIENT AND REUSABLE CATALYTIC SYSTEM OF CuI-PEG FOR N-ARYLATION OF IMIDAZOLES
    Zhang, Qiang
    Luo, Jun
    Wei, Yunyang
    [J]. SYNTHETIC COMMUNICATIONS, 2012, 42 (01) : 114 - 121
  • [6] N-arylation of indoles with aryl halides using copper/glycerol as a mild and highly efficient recyclable catalytic system
    Yadav, Dilip Kumar T.
    Rajak, Sanil S.
    Bhanage, Bhalchandra M.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (04) : 931 - 935
  • [7] A Simple and Efficient Catalytic System for N-Arylation of Imidazoles in Water
    Wang, Yi
    Wu, Zhiqing
    Wang, Lixia
    Li, Zhengkai
    Zhou, Xiangge
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) : 8971 - 8974
  • [8] Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity
    Mikhaylov, Vladimir N.
    Sorokoumov, Viktor N.
    Liakhov, Denis Martin
    Tskhovrebov, Alexander G.
    Balova, Irina A.
    [J]. CATALYSTS, 2018, 8 (04):
  • [9] Polystyrene-supported palladium(II) N,N-dimethylethylenediamine complex: A recyclable catalyst for Suzuki-Miyaura cross-coupling reactions in water
    Balaswamy, Kodicherla
    Pullaiah, Perumgani C.
    Srinivas, Keesara
    Rao, Mandapati Mohan
    [J]. INORGANICA CHIMICA ACTA, 2014, 423 : 95 - 100
  • [10] "On Water" promoted N-arylation reactions using Cu (0)/myo-inositol catalytic system
    Zhou, Qifan
    Du, Fangyu
    Chen, Yuanguang
    Fu, Yang
    Chen, Guoliang
    [J]. TETRAHEDRON LETTERS, 2019, 60 (29) : 1938 - 1941