A dinuclear copper(I) thiodiacetate complex as an efficient and reusable click' catalyst for the synthesis of glycoconjugates

被引:21
|
作者
Sareen, Neha [1 ]
Singh, Anoop S. [1 ]
Tiwari, Vinod K. [1 ]
Kant, Rajni [2 ]
Bhattacharya, Subrato [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[2] Univ Jammu, Dept Phys, Jammu 180006, India
关键词
AZIDE-ALKYNE CYCLOADDITION; CHEMISTRY INSPIRED SYNTHESIS; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; LIGANDS; FUNCTIONALITY; SURFACES;
D O I
10.1039/c7dt02346d
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We report herein the facile synthesis and structural characterization of a highly stable dinuclear Cu(I) complex, [(PPh3)(2)Cu(mu-tda) Cu(PPh3) (2)].6H(2)O 1 (tda = thiodiacetate anion), in which the Cu-Cu distance is 7.197 angstrom. This " pre-formed" complex serves as an extremely efficient and recyclable homogeneous catalyst (2 mol%, 30 min) for CuAAC in dichloromethane solvent. The synthesis of a variety of glycoconjugates under ambient conditions is successfully achieved using 1 as a catalyst. The products are obtained in high yields and very short reaction times while complying with the " click protocols". A simpler procedure solely involving the mixing of substrates with 1 (i. e. base free and solvent free) gave the corresponding glycoconjugate in 10 min using 2 mol% of the catalyst.
引用
收藏
页码:12705 / 12710
页数:6
相关论文
共 50 条
  • [1] Polymer-anchored copper(II) complex: an efficient reusable catalyst for the synthesis of propargylamines
    Kodicherla, Balaswamy
    Perumgani, Pullaiah C.
    Mandapati, Mohan Rao
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (10) : 756 - 759
  • [2] Efficient synthesis of a labile copper(I)-rotaxane complex using click chemistry
    Mobian, Pierre
    Collin, Jean-Paul
    Sauvage, Jean-Pierre
    TETRAHEDRON LETTERS, 2006, 47 (28) : 4907 - 4909
  • [3] Functionalized polytriazoles on graphene oxide-supported copper(I) complex as an effective reusable catalyst for sonochemical click synthesis of triazoles in aqueous media
    Naeimi, Hossein
    Ansarian, Zahra
    INORGANICA CHIMICA ACTA, 2017, 466 : 417 - 425
  • [4] Ionic Liquid Containing Copper(I): A New, Green, Homogeneous, and Reusable Catalyst for Click Cyclization
    Ahmady, Amanollah Zarei
    Heidarizadeh, Fariba
    Keshavarz, Mosadegh
    SYNTHETIC COMMUNICATIONS, 2013, 43 (15) : 2100 - 2109
  • [5] Polymer-Supported Azide and Copper(I): Green Reusable Reagent and Catalyst for Click Cyclization
    Albadi, Jalal
    Keshavarz, Mosadegh
    SYNTHETIC COMMUNICATIONS, 2013, 43 (15) : 2019 - 2030
  • [6] Functionalized Polystyrene Supported Copper(I) Complex as an Effective and Reusable Catalyst for Propargylamines Synthesis in Aqueous Medium
    Islam, Md. Mominul
    Roy, Anupam Singha
    Islam, Sk. Manirul
    CATALYSIS LETTERS, 2016, 146 (06) : 1128 - 1138
  • [7] Functionalized Polystyrene Supported Copper(I) Complex as an Effective and Reusable Catalyst for Propargylamines Synthesis in Aqueous Medium
    Md. Mominul Islam
    Anupam Singha Roy
    Sk. Manirul Islam
    Catalysis Letters, 2016, 146 : 1128 - 1138
  • [8] Synthesis, Crystal Structure and Properties of Dinuclear Copper(I) Complex
    Kang Wei
    Deng Zhao-Peng
    Gao Shan
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2011, 27 (04) : 655 - 658
  • [9] Synthesis, characterization and properties of a new dinuclear copper (I) complex
    Pang, Hai-Xia
    Yuan, Xi-Ming
    Wang, Xian-Wen
    He, Xiong
    Rengong Jingti Xuebao/Journal of Synthetic Crystals, 2013, 42 (12): : 2720 - 2725
  • [10] Copper-polymer nanocomposite: An efficient catalyst for green Huisgen click synthesis
    Zuraev, Alexander V.
    Grigoriev, Yuri V.
    Budevich, Vladislav A.
    Ivashkevich, Oleg A.
    TETRAHEDRON LETTERS, 2018, 59 (16) : 1583 - 1586