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Ligand-Free Copper-Catalyzed Coupling of Phenols with Nitroarenes by using a Metal–Organic Framework as a Robust and Recoverable Catalyst

Authors

  • Dr. Nam T. S. Phan,

    Corresponding author
    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Vietnam), Fax: (+84) 8-38637504
    • Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Vietnam), Fax: (+84) 8-38637504
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  • Tung T. Nguyen,

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Vietnam), Fax: (+84) 8-38637504
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  • Vu T. Nguyen,

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Vietnam), Fax: (+84) 8-38637504
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  • Khoa D. Nguyen

    1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City (Vietnam), Fax: (+84) 8-38637504
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Abstract

A highly porous metal–organic framework Cu2(BDC)2(DABCO) (H2BDC=1,4-benzenedicarboxylic acid, DABCO=1,4-diazabicyclo[2.2.2]octane) was synthesized and used as an efficient recyclable heterogeneous catalyst for the coupling reaction of phenols with nitroarenes to form diaryl ethers without using a ligand. Physical characterization of the MOF was obtained by using XRD, SEM, TEM, thermogravimetric analysis (TGA), FTIR spectroscopy, atomic absorption spectrophotometry (AAS), H2 temperature-programmed reduction (H2-TPR), and N2 physisorption measurements. The Cu2(BDC)2(DABCO)-catalyzed coupling reaction offers several advantages compared to the conventional Ullmann reaction for the synthesis of unsymmetrical diaryl ethers. To the best of our knowledge, the ligand-free Cu-catalyzed O-arylation reaction of phenols with nitroarenes that uses a heterogeneous catalyst has not been mentioned previously in the literature.

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