Ferromagnetic nanoparticle-supported copper complex: A highly efficient and reusable catalyst for three-component syntheses of 1,4-disubstituted 1,2,3-triazoles and C-S coupling of aryl halides

被引:21
|
作者
Khodaei, Mohammad Mehdi [1 ]
Bahrami, Kiumars [1 ]
Meibodi, Farhat Sadat [1 ]
机构
[1] Razi Univ, Fac Chem, Dept Organ Chem, Kermanshah 6714967346, Iran
关键词
1,2,3-triazole; C-S coupling reaction; immobilized copper catalyst; magnetic nanoparticles; terpyridines; ONE-POT SYNTHESIS; CLICK CHEMISTRY; IN-SITU; 1,3-DIPOLAR CYCLOADDITIONS; REGIOSELECTIVE SYNTHESIS; HETEROGENEOUS CATALYST; TERMINAL ALKYNES; AZIDES; THIOLS; VERSATILE;
D O I
10.1002/aoc.3714
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new nanocatalyst was synthesized by immobilization of 4'-(4-hydroxyphenyl)2,2':6', 2 ''-terpyridine/CuI complex on ferromagnetic nanoparticles through a surface modification (FMNPs@SiO2-TPy-Cu). This heterogeneous catalyst was characterized using various techniques including Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, X-ray diffraction, vibrating sample magnetometry and thermogravimetric analysis. The resulting nanocatalyst presented excellent catalytic activity for the regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles and thioethers. The thermally and chemically stable, benign and economical catalyst was easily recovered using an external magnet and reused in at least five successive runs without an appreciable loss of activity.
引用
收藏
页数:10
相关论文
共 50 条
  • [21] Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides
    Keshavarz, Mosadegh
    Iravani, Nasir
    Ghaedi, Abdolmohammad
    Ahmady, Amanollah Zarei
    Vafaei-Nezhad, Masoumeh
    Karimi, Sara
    SPRINGERPLUS, 2013, 2
  • [22] Facile Synthesis of 1,4-Disubstituted 1,2,3-Triazoles Using Tetraaza-coordinated Copper(II) Complexes as Efficient Catalysts
    Samuel, Angel Green
    Jebasingh, Bhagavathsingh
    CHEMISTRYSELECT, 2020, 5 (02): : 645 - 648
  • [23] Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition
    Pawar, Arvind
    Gajare, Shivanand
    Jagdale, Ashutosh
    Patil, Sandip
    Chandane, Wilson
    Rashinkar, Gajanan
    Patil, Suresh
    CATALYSIS LETTERS, 2022, 152 (06) : 1854 - 1868
  • [24] Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition
    Arvind Pawar
    Shivanand Gajare
    Ashutosh Jagdale
    Sandip Patil
    Wilson Chandane
    Gajanan Rashinkar
    Suresh Patil
    Catalysis Letters, 2022, 152 : 1854 - 1868
  • [25] A recyclable and water soluble copper(I)-catalyst: one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation
    Nekkanti, Shalini
    Veeramani, Karuna
    Kumari, S. Sujana
    Tokala, Ramya
    Shankaraiah, Nagula
    RSC ADVANCES, 2016, 6 (105) : 103556 - 103566
  • [26] Copper(I) oxide nanoparticles supported on magnetic casein as a bio-supported and magnetically recoverable catalyst for aqueous click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles
    Shaabani, Shabnam
    Tabatabaei, Azadeh Tavousi
    Shaabani, Ahmad
    APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (02)
  • [27] Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via 1,3-Dipolar Cycloaddition/C-N Coupling of Propargyl Alcohols/amines and Aryl Azides
    Bakherad, Mohammad
    Ghalenoei, Ahmad Kakavand
    Keivanloo, Ali
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (12) : 2683 - 2692
  • [28] Copper Nanoparticles in Polyvinyl Alcohol–Acrylic Acid Matrix: An Efficient Heterogeneous Catalyst for the Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Click Reaction
    Afsaneh Taheri Kal-Kashvandi
    Majid M. Heravi
    Shervin Ahmadi
    Tayebeh Hosseinnejad
    Journal of Inorganic and Organometallic Polymers and Materials, 2018, 28 : 1457 - 1467
  • [29] Application of magnetic nanoparticle-supported CuBr: a highly efficient and reusable catalyst for the one-pot and scale-up synthesis of 1,2,3-triazoles under microwave-assisted conditions
    Xiong, Xingquan
    Cai, Lei
    CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (05) : 1301 - 1307
  • [30] Nano magnetite supported metal ions as robust, efficient and recyclable catalysts for green synthesis of propargylamines and 1,4-disubstituted 1,2,3-triazoles in water
    Tajbakhsh, Mahmood
    Farhang, Maryam
    Baghbanian, Seyed Meysam
    Hosseinzadeh, Rahman
    Tajbakhsh, Mahghol
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) : 1827 - 1839