Synthesis, Characterization and First Application of Graphene Oxide Functionalized Cu(II) Complex for the Synthesis of 1,2,3-Triazole Derivatives

References

• X. Huang, X. Qi, F. Boey, and H. Zhang, “Graphene-Based Composites,” Chemical Society Reviews 41, no. 2 (2012): 666–86.
   PubMed Web of Science ®Google Scholar
• G. Xin, T. Yao, H. Sun, S. M. Scott, D. Shao, G. Wang, and J. Lian, “Highly Thermally Conductive and Mechanically Strong Graphene Fibers,” Science (New York, N.Y.) 349, no. 6252 (2015): 1083–7.
   PubMed Web of Science ®Google Scholar
• Dan Li, Marc B. Müller, Scott Gilje, Richard B. Kaner, and Gordon G. Wallace, “ Processable Aqueous Dispersions of Graphene Nanosheets,” Nature Nanotechnology 3, no. 2 (2008): 101–5.
   PubMed Web of Science ®Google Scholar
• G. Jo, M. Choe, S. Lee, W. Park, Y. H. Kahng, and T. Lee, “The Application of Graphene as Electrodes in Electrical and Optical Devices,” Nanotechnology 23, no. 11 (2012): 112001.
   PubMed Web of Science ®Google Scholar
• Y. Zhu, S. Murali, W. Cai, X. Li, J. W. Suk, J. R. Potts, and R. S. Ruoff, “Graphene and Graphene Oxide: synthesis, Properties, and Applications,” Advanced Materials (Deerfield Beach, FLA.) 22, no. 35 (2010): 3906–24.
   PubMed Web of Science ®Google Scholar
• Y. You, X. Jin, X. Wen, V. Sahajwalla, V. Chen, H. Bustamante, and R. Joshi, “Application of Graphene Oxide Membranes for Removal of Natural Organic Matter from Water,” Carbon 129, (2018): 415–9.
   Web of Science ®Google Scholar
• C. Chung, Y.-K. Kim, D. Shin, S.-R. Ryoo, B. H. Hong, and D.-H. Min, “Biomedical Applications of Graphene and Graphene Oxide,” Accounts of Chemical Research 46, no. 10 (2013): 2211–24.
   PubMed Web of Science ®Google Scholar
• Z. Hoseini, A. Davoodnia, A. Khojastehnezhad, and M. Pordel, “Phosphotungstic Acid Supported on Functionalized Graphene Oxide Nanosheets (GO-SiC3-NH3-H2PW): Preparation, Characterization, and First Catalytic Application in the Synthesis of Amidoalkyl Naphthols,” Eurasian Chemical Communications 2 (2020): 398–409.
   Google Scholar
• S. Eigler, S. Grimm, F. Hof, and A. Hirsch, “Graphene Oxide: A Stable Carbon Framework for Functionalization,” Journal of Materials Chemistry A 1, no. 38 (2013): 11559–62.
   Web of Science ®Google Scholar
• D.-H. Lan, Y.-X. Gong, N.-Y. Tan, S.-S. Wu, J. Shen, K.-C. Yao, B. Yi, C.-T. Au, and S.-F. Yin, “Multi-Functionalization of GO with Multi-Cationic ILs as High Efficient Metal-Free Catalyst for CO2 Cycloaddition under Mild Conditions,” Carbon 127 (2018): 245–54.
   Web of Science ®Google Scholar
• A. Khojastehnezhad, M. Bakavoli, A. Javid, M. M. K. Siuki, and F. Moeinpour, “Covalently Copper (II) Porphyrin Cross-Linked Graphene Oxide: Preparation and Catalytic Activity,” Catalysis Letters 149, no. 3 (2019): 713–22.
   Web of Science ®Google Scholar
• A. Khojastehnezhad, M. Bakavoli, A. Javid, M. M. K. Siuki, and M. Shahidzadeh, “Synthesis, Characterization, and Investigation of Catalytic Activity of Copper (II) Porphyrin Graphene Oxide for Azide–Alkyne Cycloaddition,” Research on Chemical Intermediates 45, no. 9 (2019): 4473–85.
   Web of Science ®Google Scholar
• M. Keyhaniyan, A. Shiri, H. Eshghi, and A. Khojastehnezhad, “Synthesis, Characterization and First Application of Covalently Immobilized Nickel-Porphyrin on Graphene Oxide for Suzuki Cross-Coupling Reaction,” New Journal of Chemistry 42, no. 24 (2018): 19433–41.
   Web of Science ®Google Scholar
• Z. Ghadamyari, A. Shiri, A. Khojastehnezhad, and S. M. Seyedi, “Zirconium (IV) Porphyrin Graphene Oxide: A New and Efficient Catalyst for the Synthesis of 3, 4‐Dihydropyrimidin‐2 (1H)‐Ones,” Applied Organometallic Chemistry 33, no. 9 (2019): e5091.
   Web of Science ®Google Scholar
• F. Ataie, A. Davoodnia, and A. Khojastehnezhad, “Graphene Oxide Functionalized Organic-Inorganic Hybrid (GO–Si–NH2–PMo): an Efficient and Green Catalyst for the Synthesis of Tetrahydrobenzo [b] Pyran Derivatives,” Polycyclic Aromatic Compounds. (2019): 1–14. https://doi.org/10.1080/10406638.2019.1622137
   Google Scholar
• Y. Zhu, Y. Shi, Z. Huang, L. Duan, Y. Hu, and X. Gong, “Preparation of Schiff Base Decorated Graphene Oxide and Its Application in TPU with Enhanced Thermal Stability,” RSC Advances 6, no. 93 (2016): 90018–23.
   Web of Science ®Google Scholar
• X. Zhuang, F. Zhang, D. Wu, and X. Feng, “Graphene Coupled Schiff-base Porous Polymers: Towards Nitrogen-enriched Porous Carbon Nanosheets With Ultrahigh Electrochemical Capacity,” Advanced Materials (Deerfield Beach, Fla.) 26, no. 19 (2014): 3081–6.
   PubMed Web of Science ®Google Scholar
• S. Kumari, A. Shekhar, and D. D. Pathak, “Synthesis and Characterization of a Cu (II) Schiff Base Complex Immobilized on Graphene Oxide and Its Catalytic Application in the Green Synthesis of Propargylamines,”RSC Advances 6, no. 19 (2016): 15340–4.
   Web of Science ®Google Scholar
• S. Kumari, A. Mittal, A. Kumar, and S. K. Sharma, “Palladium Nanoparticles Immobilized on Schiff Base‐Functionalized Graphene‐Oxide: Application in Carbon‐Carbon Cross‐Coupling Reactions,” ChemistrySelect 4 (2019): 10828–37.
   Web of Science ®Google Scholar
• N. Huang, S. Zhang, L. Yang, M. Liu, H. Li, Y. Zhang, and S. Yao, “Multifunctional Electrochemical Platforms Based on the Michael Addition/Schiff Base Reaction of Polydopamine Modified Reduced Graphene Oxide: Construction and Application,” ACS Applied Materials & Interfaces 7, no. 32 (2015): 17935–46.
   PubMed Web of Science ®Google Scholar
• M. Rohaniyan, A. Davoodnia, S. A. Beyramabadi, and A. Khojastehnezhad, “Phosphomolybdic Acid Supported on Schiff Base Functionalized Graphene Oxide Nanosheets: Preparation, Characterization, and First Catalytic Application in the Multi‐Component Synthesis of Tetrahydrobenzo [a] Xanthene‐11‐Ones,” Applied Organometallic Chemistry 33, no. 5 (2019): e4881.
   Web of Science ®Google Scholar
• M. Rohaniyan, A. Davoodnia, A. Khojastehnezhad, and S. A. Beyramabadi, “Catalytic Evaluation of Newly Prepared GO-SB-H2PMo as an Efficient and Reusable Nanocatalyst for the Neat Synthesis of Amidoalkyl Naphthols,” Eurasian Chemical Communications 2 (2020): 329–39.
   Google Scholar
• Z. Ghadamyari, A. Khojastehnezhad, S. M. Seyedi, and A. Shiri, “Co (II)‐Porphyrin Immobilized on Graphene Oxide: An Efficient Catalyst for the Beckmann Rearrangement,”ChemistrySelect 4, no. 36 (2019): 10920–7.
   Web of Science ®Google Scholar
• F. Raoufi, M. Monajjemi, H. Aghaei, K. Zare, and M. Ghaedi, “Preparation, Characterization and First Application of Graphene Oxide‐Metformin‐Nickel for the Suzuki Cross‐Coupling Reaction,”ChemistrySelect 5, no. 1 (2020): 211–7.
   Web of Science ®Google Scholar
• H. Su, S. Wu, Z. Li, Q. Huo, J. Guan, and Q. Kan, “Co (II), Fe (III) or VO (II) Schiff Base Metal Complexes Immobilized on Graphene Oxide for Styrene Epoxidation,”Applied Organometallic Chemistry 29, no. 7 (2015): 462–7.
   Web of Science ®Google Scholar
• R. Huisgen, “1, 3‐Dipolar Cycloadditions. Past and Future,”Angewandte Chemie International Edition in English 2, no. 10 (1963): 565–98.
   Google Scholar
• C. W. Tornøe, C. Christensen, and M. Meldal, “Peptidotriazoles on Solid phase: [1,2,3]-Triazoles by Regiospecific Copper(i)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides,” The Journal of Organic Chemistry 67no. 9 (2002): 3057–64.
   PubMed Web of Science ®Google Scholar
• V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, “A Stepwise Huisgen Cycloaddition Process: Copper (I)‐Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes,” Angewandte Chemie 114, no. 14 (2002): 2708–11.
   Google Scholar
• M. Meldal, and C. W. Tornøe, “ Cu-catalyzed Azide-alkyne Cycloaddition,” Chemical Reviews 108, no. 8 (2008): 2952–3015.
   PubMed Web of Science ®Google Scholar
• M. S. Singh, S. Chowdhury, and S. Koley, “Advances of Azide-Alkyne Cycloaddition-Click Chemistry Over the Recent Decade,” Tetrahedron 72, no. 35 (2016): 5257–83.
   Web of Science ®Google Scholar
• W. Zhang, X. He, B. Ren, Y. Jiang, and Z. Hu, “Cu (OAc) 2· H2O—an Efficient Catalyst for Huisgen-Click Reaction in Supercritical Carbon Dioxide,” Tetrahedron Letters. 56, no. 19 (2015): 2472–5.
   Web of Science ®Google Scholar
• A. A. Ali, M. Chetia, and D. Sarma, “Urea Assisted Copper (I)-Catalyzed Azide–Alkyne Cycloaddition Reactions in Water,” Tetrahedron Letters. 57, no. 15 (2016): 1711–4.
   Web of Science ®Google Scholar
• K. Pericherla, A. Jha, B. Khungar, and A. Kumar, “ Copper-catalyzed Tandem Azide-alkyne Cycloaddition, Ullmann Type C-N Coupling, and Intramolecular Direct Arylation,” Organic Letters 15, no. 17 (2013): 4304–7.
   PubMed Web of Science ®Google Scholar
• V. O. Rodionov, V. V. Fokin, and M. Finn, “Mechanism of the Ligand‐Free CuI‐Catalyzed Azide–Alkyne Cycloaddition Reaction,” Angewandte Chemie 117, no. 15 (2005): 2250–5.
   Google Scholar
• Y.-J. Song, C.-Y. Yoo, J.-T. Hong, S.-J. Kim, S.-U. Son, and H.-Y. Jang, “Nanocrystalline Copper Oxide (II)-Catalyzed Alkyne-Azide Cycloadditions,” Bulletin of the Korean Chemical Society. 29, (2008) : 1561–4.
   Web of Science ®Google Scholar
• R. P. Jumde, C. Evangelisti, A. Mandoli, N. Scotti, and R. Psaro, “Aminopropyl-Silica-Supported Cu Nanoparticles: An Efficient Catalyst for Continuous-Flow Huisgen Azide-Alkyne Cycloaddition (CuAAC),” Journal of Catalysis 324 (2015): 25–31.
   Web of Science ®Google Scholar
• L. Mohammadi, M. A. Zolfigol, A. Khazaei, M. Yarie, S. Ansari, S. Azizian, and M. Khosravi, “Synthesis of Nanomagnetic Supported Thiourea–Copper (I) Catalyst and Its Application in the Synthesis of Triazoles and Benzamides,” Applied Organometallic Chemistry 32, no. 1 (2018): e3933.
   Web of Science ®Google Scholar
• M. K. Barman, A. K. Sinha, and S. Nembenna, “An Efficient and Recyclable Thiourea-Supported Copper (I) chloride Catalyst for Azide–Alkyne Cycloaddition Reactions,” Green Chemistry 18, no. 8 (2016): 2534–41.
   Web of Science ®Google Scholar
• H. Sharghi, R. Khalifeh, and M. M. Doroodmand, “Copper Nanoparticles on Charcoal for Multicomponent Catalytic Synthesis of 1, 2, 3‐Triazole Derivatives from Benzyl Halides or Alkyl Halides, Terminal Alkynes and Sodium Azide in Water as a “Green” Solvent,” Advanced Synthesis & Catalysis 351, no. 1–2 (2009): 207–18.
   Web of Science ®Google Scholar
• Z. Ghadamyari, A. Khojastehnezhad, S. M. Seyedi, F. Taghavi, and A. Shiri, “Graphene Oxide Functionalized Zn (II) Salen Complex: An Efficient and New Route for the Synthesis of 1, 2, 3‐Triazole Derivatives,” ChemistrySelect 5, no. 33 (2020): 10233–42.
   Web of Science ®Google Scholar
• M. Chetia, M. Konwar, B. Pegu, S. Konwer, and D. Sarma, “Synthesis of Copper Containing Polyaniline Composites through Interfacial Polymerisation: An Effective Catalyst for Click Reaction at Room Temperature,” Journal of Molecular Structure 1233, (2021) : 130019.
   Web of Science ®Google Scholar
• M. B. M. Krishna, N. Venkatramaiah, R. Venkatesan, and D. N. Rao, “Synthesis and Structural, Spectroscopic and Nonlinear Optical Measurements of Graphene Oxide and Its Composites with Metal and Metal Free Porphyrins,” Journal of Materials Chemistry 22, no. 7 (2012): 3059–68.
   Web of Science ®Google Scholar
• S. Hemmati, L. Mehrazin, M. Pirhayati, and H. Veisi, “Immobilization of Palladium Nanoparticles on Metformin-Functionalized Graphene Oxide as a Heterogeneous and Recyclable Nanocatalyst for Suzuki Coupling Reactions and Reduction of 4-Nitrophenol,” Polyhedron 158 (2019): 414–22.
   Web of Science ®Google Scholar
• P. Bhanja, S. K. Das, A. K. Patra, and A. Bhaumik, “Functionalized Graphene Oxide as an Efficient Adsorbent for CO 2 Capture and Support for Heterogeneous Catalysis,”RSC Advances 6, no. 76 (2016): 72055–68.
   Web of Science ®Google Scholar
• M. Celebi, K. Karakas, I. E. Ertas, M. Kaya, and M. Zahmakiran, “Palladium Nanoparticles Decorated Graphene Oxide: active and Reusable Nanocatalyst for the Catalytic Reduction of Hexavalent Chromium (VI),”ChemistrySelect 2, no. 27 (2017): 8312–9.
   Web of Science ®Google Scholar
• R. Betancourt-Galindo, P. Reyes-Rodriguez, B. Puente-Urbina, C. Avila-Orta, O. Rodríguez-Fernández, G. Cadenas-Pliego, R. Lira-Saldivar, and L. García-Cerda, “Synthesis of Copper Nanoparticles by Thermal Decomposition and Their Antimicrobial Properties,” Journal of Nanomaterials 2014, (2014): 1–5. ).
   Web of Science ®Google Scholar
• F. Deng, X. Pei, Y. Luo, X. Luo, D. D. Dionysiou, S. Wu, and S. Luo, “Fabrication of Hierarchically Porous Reduced Graphene Oxide/SnIn4S8 Composites by a Low-Temperature co-Precipitation Strategy and Their Excellent Visible-Light Photocatalytic Mineralization Performance,” Catalysts 6, no. 8 (2016): 113.
   Web of Science ®Google Scholar
• H. Sharghi, P. Shiri, and M. Aberi, “Five-Membered N-Heterocycles Synthesis Catalyzed by Nano-Silica Supported Copper (II)–2-Imino-1, 2-Diphenylethan-1-ol Complex,” Catalysis Letters 147, no. 11 (2017): 2844–62.
   Web of Science ®Google Scholar
• Z. X. Wang, and Z. G. Zhao, “Synthesis of 1, 4‐Disubstituted 1, 2, 3‐Triazoles via a Three‐Component Reaction in Water in the Presence of Cux (X = Cl, I,” Journal of Heterocyclic Chemistry 44, no. 1 (2007): 89–92.
   Web of Science ®Google Scholar
• Z. Hasanpour, A. Maleki, M. Hosseini, L. Gorgannezhad, V. Nejadshafiee, A. Ramazani, I. Haririan, A. Shafiee, and M. Khoobi, “Efficient Multicomponent Synthesis of 1, 2, 3-Triazoles Catalyzed by Cu (II) Supported on PEI@ Fe3O4 MNPs in a Water/PEG 300 System,” Turkish Journal of Chemistry 41, no. 2 (2017): 294–307.
   Web of Science ®Google Scholar
• M. Chetia, P. S. Gehlot, A. Kumar, and D. Sarma, “A Recyclable/Reusable Hydrotalcite Supported Copper Nano Catalyst for 1, 4-Disubstituted-1, 2, 3-Triazole Synthesis via Click Chemistry Approach,” Tetrahedron Letters 59, no. 4 (2018): 397–401.
   Web of Science ®Google Scholar
• M. Chetia, A. A. Ali, D. Bhuyan, L. Saikia, and D. Sarma, “Magnetically Recoverable Chitosan-Stabilised Copper–Iron Oxide Nanocomposite Material as an Efficient Heterogeneous Catalyst for Azide–Alkyne Cycloaddition Reactions,” New Journal of Chemistry 39, no. 8 (2015): 5902–7.
   Web of Science ®Google Scholar
• Nubia Boechat, Vitor F. Ferreira, Sabrina B. Ferreira, Maria de Lourdes G Ferreira, Fernando de C da Silva, Monica M. Bastos, Marilia Dos S Costa, Maria Cristina S. Lourenço, Angelo C. Pinto, Antoniana U. Krettli, et al. “Novel 1,2,3-Triazole Derivatives for Use Against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain,” Journal of Medicinal Chemistry 54, no. 17 (2011): 5988–99.
   PubMed Web of Science ®Google Scholar
• A. A. Ali, M. Chetia, P. J. Saikia, and D. Sarma, (“DHQD) 2 PHAL Ligand-Accelerated Cu-Catalyzed Azide–Alkyne Cycloaddition Reactions in Water at Room Temperature,” RSC Advances. 4, no. 110 (2014): 64388–92.
   Web of Science ®Google Scholar
• N. Almirante, S. Cicardi, C. Napoletano, and M. Serravalle, “Dihydro Azoles and Free Radicals: Part I. 1-Aryl-4-Methylene-5-Morpholino-v-Triazolines and Halomethyl Radicals: fragmentation of Triazolinic Radical Sigma Complexes,” Tetrahedron 43, no. 3 (1987): 625–30.
   Web of Science ®Google Scholar
• L. Liang, and D. Astruc, “The Copper (I)-Catalyzed Alkyne-Azide Cycloaddition (CuAAC)“Click” Reaction and Its Applications. An Overview, Coordination,” Chemical Reviews 255, no. 23/24 (2011): 2933–45.
   Google Scholar
• K. Namitharan, M. Kumarraja, and K. Pitchumani, “ Cu(II)-hydrotalcite as an efficient heterogeneous catalyst for Huisgen [3 + 2] cycloaddition,” Chemistry (Weinheim an Der Bergstrasse, Germany) 15, no. 12 (2009): 2755–8.
   PubMed Web of Science ®Google Scholar
• D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, and B. Chen, “Solvent-Free Synthesis of 1, 4-Disubstituted 1, 2, 3-Triazoles Using a Low Amount of Cu (PPh3)2 NO3 Complex,” Green Chemistry 12, no. 12 (2010): 2120–3.
   Web of Science ®Google Scholar
• P. Veerakumar, M. Velayudham, K.-L. Lu, and S. Rajagopal, “Highly Dispersed Silica-Supported Nanocopper as an Efficient Heterogeneous Catalyst: application in the Synthesis of 1, 2, 3-Triazoles and Thioethers,” Catalysis Science & Technology 1, no. 8 (2011): 1512–25.
   Web of Science ®Google Scholar