Zinc (II) complex immobilized on the surface of magnetic nanoparticles modified with phenanthroline: A novel and efficient nanomagnetic reusable catalyst for cross-coupling reaction of aryl iodides with terminal aromatic alkynes

References

• Kaur, H.; Garg, N. Interactive Effects of Zinc-Arbuscular Mycorrhizal (AM) Fungi on Cadmium Uptake, Rubisco, Osmolyte Synthesis and Yield in Cajanus cajan (L.) Millsp. Int. J. Sustain. Agric. Res. 2021, 8, 17–42. DOI: https://doi.org/10.18488/journal.70.2021.81.17.42.
   Google Scholar
• Lakshman, M. Fe3O4@SiO2-Pip-SA Nanocomposite: A Novel and Highly Efficient Reusable Acidic Catalyst for Synthesis of Rhodanine Derivatives. J. Synth. Chem. 2022, 1, 48–51. DOI: https://doi.org/10.22034/jsc.2022.149234.
   Google Scholar
• Mikhailov, O. V.; Chachkov, D. V. Novel Oxidation Degree-Zn + 3 in the Macrocyclic Compound with Trans-di[Benzo]Porphyrazine and Fluoride Ligand: Quantum-Chemical Consideration. ECB. 2020, 9, 160–163. DOI: https://doi.org/10.17628/ecb.2020.9.160-163.
   Google Scholar
• Bakhshkandi, R.; Ghoranneviss, M. Investigating the Synthesis and Growth of Titanium Dioxide Nanoparticles on a Cobalt Catalyst. JRSET. 2020, 7, 1–3. DOI: https://doi.org/10.24200/jrset.vol7iss4pp1-3.
   Google Scholar
• Gharibzadeh, F.; Vessally, E.; Edjlali, L.; et al. A DFT Study on Sumanene, Corannulene and Nanosheet as the Anodes in Li − Ion Batteries. Iran. J. Chem. Chem. Eng. 2020, 39, 51–62. DOI: https://doi.org/10.30492/ijcce.2020.106867.3568.
   Web of Science ®Google Scholar
• Netam, a.; Bhargava, V.; Singh, R.; Sharma, P. Physico-Chemical Characterization of Ayurvedic Swarna Bhasma by Using SEM, EDAX, XRD and PSA. J. Complement. Med. Res. 2021, 12, 204. DOI: https://doi.org/10.5455/jcmr.2021.12.02.23.
   Web of Science ®Google Scholar
• Gupta, S. Sulfuric Acid Heterogenized on Magnetic Nanoparticles Functionalized with Glycerol Catalyzed Synthesis of 2, 3-Dihydroquinazoline-4(1H)-Ones. J. Synth. Chem. 2022, 1, 37–41. DOI: https://doi.org/10.22034/jsc.2022.149222.
   Google Scholar
• Nair, K.; Velmurugan, R.; Sukumaran, S. Influence of Polylactic Acid and Polycaprolactone on Dissolution Characteristics of Ansamycin-Loaded Polymeric Nanoparticles: An Unsatisfied Attempt for Drug Release Profile. J. Pharm. Negative Results 2020, 11, 23. DOI: https://doi.org/10.4103/jpnr.JPNR_26_19.
   Web of Science ®Google Scholar
• Mohan, R.; Ganapathy, K.; Rama, A. Brain Tumour Classification of Magnetic Resonance Images Using a Novel CNN Based Medical Image Analysis and Detection Network in Comparison with VGG16. J. Popul. Ther. Clin. Pharmacol. 2022, 28, e113–e125. DOI: https://doi.org/10.47750/jptcp.2022.873.
   PubMed Web of Science ®Google Scholar
• Blagojević, D.; Lazić, D.; Kešelj, D.; et al. Determining the Content of Silicon Dioxide in Bauxites Using X-Ray Fluorescence Spectrometry. Iran. J. Chem. Chem. Eng. 2019, 38, 115–125.
   Google Scholar
• Saied, S. M.; Mohammed, S. J.; Khaleel, B. T.; Saleh, M. Y. Comparative Studies between Conventional Techniques and Green Chemistry to Synthesis of Novel Piperidinium Salts Ionic Liquids (PBSILs). J. Chem. Heal. Risks 2021, 11, 451–456. DOI: https://doi.org/10.22034/JCHR.2021.686640.
   Google Scholar
• Zouaoui, E. H.; Djamel, N.; Wan Ba Karim Ghani, W. A.; Amokarane, S. High-Pressure CO2 Adsorption onto Nax Zeolite: Effect of Li+, K+, Mg2+, and Zn2+ and Equilibrium Isotherms Study. Iran. J. Chem. Chem. Eng. 2021, 40, 1195–1215. DOI: https://doi.org/10.30492/ijcce.2020.40342.
   Web of Science ®Google Scholar
• Riedel, W.; Thum, L.; Möser, J.; Fleischer, V.; Simon, U.; Siemensmeyer, K.; Schnegg, A.; Schomäcker, R.; Risse, T.; Dinse, K.-P.; et al. Magnetic Properties of Reduced and Reoxidized Mn-Na2WO4/SiO2: A Catalyst for Oxidative Coupling of Methane (OCM). J. Phys. Chem. C 2018, 122, 22605–22614. DOI: https://doi.org/10.1021/acs.jpcc.8b07386.
   Web of Science ®Google Scholar
• Heydari, Z.; Bahadorikhalili, S.; Ranjbar, P. R.; Mahdavi, M. DABCO-Modified Super-Paramagnetic Nanoparticles as an Efficient and Water-Compatible Catalyst for the Synthesis of Pyrano[3,2-c:5,6-c′]Dichromene-6,8-Dione Derivatives under Mild Reaction Conditions. Appl. Organomet. Chem. 2018, 32, e4561. DOI: https://doi.org/10.1002/aoc.4561.
   Web of Science ®Google Scholar
• Jahangirian, H.; Lemraski, E. G.; Webster, T. J.; Rafiee-Moghaddam, R.; Abdollahi, Y. A Review of Drug Delivery Systems Based on Nanotechnology and Green Chemistry: Green Nanomedicine. Int. J. Nanomedicine 2017, 12, 2957–2978. DOI: https://doi.org/10.2147/IJN.S127683.
   PubMed Web of Science ®Google Scholar
• Veisi, H.; Ghorbani, F. Iron Oxide Nanoparticles Coated with Green Tea Extract as a Novel Magnetite Reductant and Stabilizer Sorbent for Silver Ions: Synthetic Application of Fe3O4@Green Tea/Ag Nanoparticles as Magnetically Separable and Reusable Nanocatalyst for Reduction of 4. Appl. Organomet. Chem. 2017, 31, e3711. DOI: https://doi.org/10.1002/aoc.3711.
   Web of Science ®Google Scholar
• Krishnan, S. G.; Pua, F.-L.; Zhang, F. A Review of Magnetic Solid Catalyst Development for Sustainable Biodiesel Production. Biomass Bioenergy 2021, 149, 106099. DOI: https://doi.org/10.1016/j.biombioe.2021.106099.
   Web of Science ®Google Scholar
• Zhou, S.-M.; Wang, G.-Z.; Chen, H.-F.; et al. Research Progress on Heterogeneous Persulfate-Based Catalytic Materials. Xiandai Huagong/Modern Chem. Ind. 2020, 40, 20–25. DOI: https://doi.org/10.16606/j.cnki.issn0253-4320.2020.10.005.
   Google Scholar
• Xu, Y.; Cao, M.; Zhang, Q. Recent Advances and Perspective on Heterogeneous Catalysis Using Metals and Oxide Nanocrystals. Mater. Chem. Front. 2021, 5, 151–222. DOI: https://doi.org/10.1039/D0QM00549E.
   Web of Science ®Google Scholar
• Geng, W.; Wang, L.; Yang, X.-Y. Nanocell Hybrids for Green Chemistry. Trends Biotechnol. 2022, 40, In Press. DOI: https://doi.org/10.1016/j.tibtech.2022.01.012.
   PubMed Web of Science ®Google Scholar
• Masunga, N.; Mmelesi, O. K.; Kefeni, K. K.; Mamba, B. B. Recent Advances in Copper Ferrite Nanoparticles and Nanocomposites Synthesis, Magnetic Properties and Application in Water Treatment: Review. J. Environ. Chem. Eng. 2019, 7, 103179. DOI: https://doi.org/10.1016/j.jece.2019.103179.
   Web of Science ®Google Scholar
• Gholinejad, M. Palladium Nanoparticles Supported on Agarose-Catalyzed Heck-Matsuda and Suzuki-Miyaura Coupling Reactions Using Aryl Diazonium Salts. Appl. Organometal. Chem. 2013, 27, 19–22. DOI: https://doi.org/10.1002/aoc.2932.
   Web of Science ®Google Scholar
• Sharma, R. K.; Katiyar, D. Recent Advances in Transition-Metal-Catalyzed Synthesis of Coumarins. Synthesis 2016, 48, 2303–2322. DOI: https://doi.org/10.1055/s-0035-1560450.
   Web of Science ®Google Scholar
• Taheri Kal Koshvandi, A.; Heravi, M. M.; Momeni, T. Current Applications of Suzuki–Miyaura Coupling Reaction in the Total Synthesis of Natural Products: An Update. Appl. Organometal. Chem. 2018, 32, e4210. DOI: https://doi.org/10.1002/aoc.4210.
   Web of Science ®Google Scholar
• Floriani, C. Metal-Carbon and Carbon-Carbon Bond Formation from Small Molecules and One Carbon Functional Groups. Pure Appl. Chem. 1982, 54, 59–64. DOI: https://doi.org/10.1351/pac198254010059.
   Web of Science ®Google Scholar
• Miyaura, N. Cross-Coupling Reaction of Organoboron Compounds via Base-Assisted Transmetalation to Palladium(II) Complexes. J. Organomet. Chem. 2002, 653, 54–57. DOI: https://doi.org/10.1016/S0022-328X(02)01264-0.
   Web of Science ®Google Scholar
• Aly, H. M. Synthesis of Bifunctional Thieno[3,2-c]Pyrazole, Pyrazolothieno[2,3-d]Pyrimidin Derivatives and Their Antimicrobial Activities. J. Iran. Chem. Soc. 2016, 13, 999–1009. DOI: https://doi.org/10.1007/s13738-016-0813-2.
   Web of Science ®Google Scholar
• Mio, M. J. How the Principles of Green Chemistry Changed the Way Organic Chemistry Labs Are Taught at the University of Detroit Mercy. Phys. Sci. Rev. 2017, 2, 1–5. DOI: https://doi.org/10.1515/psr-2016-0077.
   Google Scholar
• Adib, M.; Yasaei, Z.; Karimi-Nami, R.; Khakyzadeh, V.; Veisi, H. Facile Preparation of Highly Stable and Active Hybrid Palladium Nanoparticles: Effectual, Reusable and Heterogeneous Catalyst for Coupling Reactions. Appl. Organometal. Chem. 2016, 30, 748–752. DOI: https://doi.org/10.1002/aoc.3499.
   Web of Science ®Google Scholar
• Wilson, M.; Kore, R.; Fraser, R. C.; Beaumont, S. K.; Srivastava, R.; Badyal, J. P. S. Recyclable Palladium Catalyst Cloths for Carbon-Carbon Coupling Reactions. Colloids Surf. A Physicochem. Eng. Asp. 2017, 520, 788–795. DOI: https://doi.org/10.1016/j.colsurfa.2017.01.050.
   Web of Science ®Google Scholar
• Chinchilla, R.; Nájera, C. The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry. Chem. Rev. 2007, 107, 874–922. DOI: https://doi.org/10.1021/cr050992x.
   PubMed Web of Science ®Google Scholar
• Govan, J.; Gun'ko, Y. K. Recent Advances in the Application of Magnetic Nanoparticles as a Support for Homogeneous Catalysts. Nanomaterials 2014, 4, 222–241. DOI: https://doi.org/10.3390/nano4020222.
   Web of Science ®Google Scholar
• Amblard, F.; Cho, J. H.; Schinazi, R. F. Cu(l)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry. Chem. Rev. 2009, 109, 4207–4220. DOI: https://doi.org/10.1021/cr9001462.
   PubMed Web of Science ®Google Scholar
• Taheri, N.; Heidarizadeh, F.; Kiasat, A. A New Magnetically Recoverable Catalyst Promoting the Synthesis of 1,4-Dihydropyridine and Polyhydroquinoline Derivatives via the Hantzsch Condensation under Solvent-Free Conditions. J. Magn. Magn. Mater. 2017, 428, 481–487. DOI: https://doi.org/10.1016/j.jmmm.2016.09.099.
   Web of Science ®Google Scholar
• Tamoradi, T.; Ghorbani-Choghamarani, A.; Ghadermazi, M. Synthesis of a New Pd(0)-Complex Supported on Magnetic Nanoparticles and Study of Its Catalytic Activity for Suzuki and Stille Reactions and Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives. Polyhedron 2018, 145, 120–130. DOI: https://doi.org/10.1016/j.poly.2018.01.016.
   Web of Science ®Google Scholar
• Soleimani, E.; Naderi Namivandi, M.; Sepahvand, H. ZnCl2 Supported on Fe3O4@SiO2 Core–Shell Nanocatalyst for the Synthesis of Quinolines via Friedländer Synthesis under Solvent-Free Condition. Appl. Organometal. Chem. 2017, 31, e3566. DOI: https://doi.org/10.1002/aoc.3566.
   Web of Science ®Google Scholar
• Ali Ghasemzadeh, M.; Elyasi, Z.; Azimi-Nasrabad, M.; Mirhosseini-Eshkevari, B. Magnetite Nanoparticles-Supported APTES as a Powerful and Recoverable Nanocatalyst for the Preparation of 2-Amino-5,10-Dihydro-5,10-Dioxo-4H-Benzo[g]Chromenes and Tetrahydrobenzo[g]Quinoline-5,10-Diones. Comb. Chem. High Throughput Screen. 2017, 20, 64–76. DOI: https://doi.org/10.2174/1386207319666161223121612.
   PubMed Web of Science ®Google Scholar
• Thankachan, A. P.; Abi, T. G.; Sindhu, K. S.; Anilkumar, G. Experimental and Mechanistic Exploration of Zn-Catalyzed Sonogashira-Type Cross-Coupling Reactions. ChemistrySelect 2016, 1, 3405–3412. DOI: https://doi.org/10.1002/slct.201600668.
   Web of Science ®Google Scholar
• Rossy, C.; Majimel, J.; Delapierre, M. T.; Fouquet, E.; Felpin, F.-X. On the Peculiar Recycling Properties of Charcoal-Supported Palladium Oxide Nanoparticles in Sonogashira Reactions. Appl. Catal. A Gen. 2014, 482, 157–162. DOI: https://doi.org/10.1016/j.apcata.2014.05.019.
   Web of Science ®Google Scholar
• Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Formation of Aryl–Nitrogen, Aryl–Oxygen, and Aryl–Carbon Bonds Using Well-Defined Copper(I)-Based Catalysts. Org. Lett. 2001, 3, 4315–4317. DOI: https://doi.org/10.1021/ol0170105.
   PubMed Web of Science ®Google Scholar
• Komáromi, A.; Tolnai, G. L.; Novák, Z. Copper-Free Sonogashira Coupling in Amine–Water Solvent Mixtures. Tetrahedron Lett. 2008, 49, 7294–7298. DOI: https://doi.org/10.1016/j.tetlet.2008.10.037.
   Web of Science ®Google Scholar
• Sabounchei, S. J.; Ahmadi, M. An Efficient Protocol for Copper- and Amine-Free Sonogashira Reactions Catalyzed by Mononuclear Palladacycle Complexes Containing Bidentate Phosphine Ligands. Catal. Commun. 2013, 37, 114–121. DOI: https://doi.org/10.1016/j.catcom.2013.03.028.
   Web of Science ®Google Scholar