Coupling reaction of aryl halides with phenylboronic acid using chitosan-copper (II) complex extracted from Persian Gulf shrimp shell

Document Type : Original Article

Authors

1 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran

2 Department of Chemistry, Shiraz University, Shiraz 7194684795, I.R. Iran

Abstract

In this research, using a suitable method and in line with the development of green chemistry, chitosan particles were prepared through the process of deacetylation from Persian Gulf shrimp shell waste, and then a copper-based complex was successfully synthesized on a substrate of chitosan particles, and with Techniques such as Fourier Transform Infrared Spectrometry (FT-IR), X-ray Diffraction (XRD), Scanning Electron Microscopy (SEM), X-ray Energy Diffraction Spectroscopy (EDX), Elemental Mapping, and Visible-Ultraviolet Spectroscopy (UV-Vis) was investigated. A wide variety of biaryl compounds were successfully synthesized through the developed catalytic process. The use of chitosan-copper (II) complex catalyst in the synthesis of biphenyl derivatives showed several advantages, including mild reaction conditions and short synthesis time, significant efficiency, avoiding the production of toxic waste, and easy separation of the catalyst. Furthermore, the chitosan-copper(II) complex was easily recovered by filtration and could be reused for five cycles without losing its structural integrity and catalytic activity.

Keywords

Main Subjects

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

References

[1] Azmana, M., Mahmood, S., Hilles, A. R., Rahman, A., Arifin, M. A. B., & Ahmed, S. (2021). A review on chitosan and chitosan-based bionanocomposites: Promising material for combatting global issues and its applications. International journal of biological macromolecules, 185, 832-848.
[2] Divya, K., & Jisha, M. S. (2018). Chitosan nanoparticles preparation and applications. Environmental chemistry letters, 16, 101-112.
[3] Keshipour, S., Ahmadi, F., Seyyedi, B., & Habibi, E. (2018). Chitosan modified with cobalt (II) as a green catalyst for the oxidation of styrene to styrene oxide. Applied Chemistry, 13(48), 67-74.
[4] Ghafuri, H., Hanifehnejad, P., & Felfelian, Z. (2023). Synthesis and characterization of porphyrin-modified chitosan biopolymer and its application in the degradation of methylene blue under visible light. Applied Chemistry.
[5] de Alvarenga, E. S. (2011). Characterization and properties of chitosan. Biotechnology of biopolymers, 91, 48-53.
[6] Wang, W., Xue, C., & Mao, X. (2020). Chitosan: Structural modification, biological activity and application. International Journal of Biological Macromolecules, 164, 4532-4546.
[7] Aranaz, I., Alcántara, A. R., Civera, M. C., Arias, C., Elorza, B., Heras Caballero, A., & Acosta, N. (2021). Chitosan: An overview of its properties and applications. Polymers, 13(19), 3256.
[8] Wang, W., Meng, Q., Li, Q., Liu, J., Zhou, M., Jin, Z., & Zhao, K. (2020). Chitosan derivatives and their application in biomedicine. International journal of molecular sciences, 21(2), 487.
[9] Ali, A., & Ahmed, S. (2018). A review on chitosan and its nanocomposites in drug delivery. International journal of biological macromolecules, 109, 273-286.
[10] Bansal, V., Sharma, P. K., Sharma, N., Pal, O. P., & Malviya, R. (2011). Applications of chitosan and chitosan derivatives in drug delivery. Advances in Biological Research, 5(1), 28-37.
[11] Guibal, E. (2004). Interactions of metal ions with chitosan-based sorbents: a review. Separation and purification technology, 38(1), 43-74.
[12] Lima, I. S., & Airoldi, C. (2003). Interaction of copper with chitosan and succinic anhydride derivative—a factorial design evaluation of the chemisorption process. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 229(1-3), 129-136.
[13] Faúndez, G., Troncoso, M., Navarrete, P., & Figueroa, G. (2004). Antimicrobial activity of copper surfaces against suspensions of Salmonella enterica and Campylobacter jejuni. BMC microbiology, 4, 1-7.
[14] Yin, X., Zhang, X., Lin, Q., Feng, Y., Yu, W., & Zhang, Q. (2004). Metal-coordinating controlled oxidative degradation of chitosan and antioxidant activity of chitosan-metal complex. Arkivoc, 9, 66-78.
[15] Buskes, M. J., & Blanco, M. J. (2020). Impact of cross-coupling reactions in drug discovery and development. Molecules, 25(15), 3493.
[16] Reeves, E. K., Entz, E. D., & Neufeldt, S. R. (2021). Chemodivergence between Electrophiles in Cross‐Coupling Reactions. Chemistry–A European Journal, 27(20), 6161-6177.
[17] Hosseini-Sarvari, M., & Dehghani, A. (2023). Nickel/TiO2-catalyzed Suzuki–Miyaura cross-coupling of arylboronic acids with aryl halides in MeOH/H2O. Monatshefte für Chemie-Chemical Monthly, 1-9.
[18] Kadu, B. S. (2021). Suzuki–Miyaura cross coupling reaction: recent advancements in catalysis and organic synthesis. Catalysis Science & Technology, 11(4), 1186-1221.
[19] Hekmati, M., Yousefi, M., Ziyadi, H., Ghasemi, E., Safari Mehr, P., Veisi, H., & Maleki, B. (2021). catalytic applications of coated nanopalladium particles coated on modified GO by Thymbraspicata extract in Suzuki coupling reactions. Applied Chemistry, 16(58), 233-244.
[20] Matsuo, K., Kuriyama, M., Yamamoto, K., Demizu, Y., Nishida, K., & Onomura, O. (2021). Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents. Synthesis, 53(23), 4449-4460.
[21] Kaboudin, B., Salemi, H., Mostafalu, R., Kazemi, F., & Yokomatsu, T. (2016). Pd (II)-β-cyclodextrin complex: Synthesis, characterization and efficient nanocatalyst for the selective Suzuki-Miyaura coupling reaction in water. Journal of organometallic chemistry, 818, 195-199.
[22] Guo, D., Shi, W., & Zou, G. (2022). Suzuki coupling of activated aryltriazenes for practical synthesis of biaryls from anilines. Advanced Synthesis & Catalysis, 364(14), 2438-2442.
[23] Tsubouchi, A., Muramatsu, D., & Takeda, T. (2013). Copper (I)‐Catalyzed Alkylation of Aryl‐and Alkenylsilanes Activated by Intramolecular Coordination of an Alkoxide. Angewandte Chemie International Edition, 52(48), 12719-12722.
[24] Sabounchei, S. J., Hashemi, A., Sedghi, A., Bayat, M., Bagherjeri, F. A., & Gable, R. W. (2017). Pd (II) and Pt (II) complexes of α-keto stabilized sulfur ylide: Synthesis, structural, theoretical and catalytic activity studies. Journal of Molecular Structure, 1135, 174-185.
[25] Ebrahimian, M. R., Tavakolian, M., & Hosseini-Sarvari, M. (2023). From Expired Metformin Drug to Nanoporous N-doped-g-C3N4: Durable Sunlight-Responsive Photocatalyst for Oxidation of Furfural to Maleic acid. Journal of Environmental Chemical Engineering, 109347.
[26] Maeda, K., Matsubara, R., & Hayashi, M. (2021). Synthesis of substituted anilines from cyclohexanones using Pd/C–ethylene system and its application to indole Synthesis. Organic Letters, 23(5), 1530-1534.
[27] Mekahlia, S., & Bouzid, B. (2009). Chitosan-Copper (II) complex as antibacterial agent: synthesis, characterization and coordinating bond-activity correlation study. Physics Procedia, 2(3), 1045-1053.
[28] Zahedi, S., Ghomi, J. S., & Shahbazi-Alavi, H. (2018). Preparation of chitosan nanoparticles from shrimp shells and investigation of its catalytic effect in diastereoselective synthesis of dihydropyrroles. Ultrasonics Sonochemistry, 40, 260-264.
[29] Da Silva, K. P. (2004). Copper sorption from diesel oil on chitin and chitosan polymers. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 237(1-3), 15-21.
[30] Usman, M. S., Zowalaty, M. E. E., Shameli, K., Zainuddin, N., Salama, M., & Ibrahim, N. A. (2013). Synthesis, characterization, and antimicrobial properties of copper nanoparticles. International journal of nanomedicine, 4467-4479.
[31] Wu, S. H., & Chen, D. H. (2004). Synthesis of high-concentration Cu nanoparticles in aqueous CTAB solutions. Journal of colloid and interface science, 273(1), 165-169.
[32] Affrose, A., Suresh, P., Azath, I. A., & Pitchumani, K. (2015). Palladium nanoparticles embedded on thiourea-modified chitosan: A green and sustainable heterogeneous catalyst for the Suzuki reaction in water. RSC Advances, 5(35), 27533-27539.
[33] Makhubela, B. C., Jardine, A., & Smith, G. S. (2011). Pd nanosized particles supported on chitosan and 6-deoxy-6-amino chitosan as recyclable catalysts for Suzuki–Miyaura and Heck cross-coupling reactions. Applied Catalysis A: General, 393(1-2), 231-241.
[34] Hajipour, A. R., & Abolfathi, P. (2017). Novel triazole-modified chitosan@ nickel nanoparticles: efficient and recoverable catalysts for Suzuki reaction. New Journal of Chemistry, 41(6), 2386-2391.
[35] Veisi, H., Ghadermazi, M., & Naderi, A. (2016). Biguanidine‐functionalized chitosan to immobilize palladium nanoparticles as a novel, efficient and recyclable heterogeneous nanocatalyst for Suzuki–Miyaura coupling reactions. Applied Organometallic Chemistry, 30(5), 341-345.
[36] Veisi, H., Ozturk, T., Karmakar, B., Tamoradi, T., & Hemmati, S. (2020). In situ decorated Pd NPs on chitosan-encapsulated Fe3O4/SiO2-NH2 as magnetic catalyst in Suzuki-Miyaura coupling and 4-nitrophenol reduction. Carbohydrate polymers, 235, 115966.
[37] Çalışkan, M., & Baran, T. (2021). Decorated palladium nanoparticles on chitosan/δ-FeOOH microspheres: A highly active and recyclable catalyst for Suzuki coupling reaction and cyanation of aryl halides. International Journal of Biological Macromolecules, 174, 120-133.
[38] Veisi, H., Najafi, S., & Hemmati, S. (2018). Pd (II)/Pd (0) anchored to magnetic nanoparticles (Fe3O4) modified with biguanidine-chitosan polymer as a novel nanocatalyst for Suzuki-Miyaura coupling reactions. International journal of biological macromolecules, 113, 186-194.
[39] Wang, G., Lv, K., Chen, T., Chen, Z., & Hu, J. (2021). Immobilizing of palladium on melamine functionalized magnetic chitosan beads: A versatile catalyst for p-nitrophenol reduction and Suzuki reaction in aqueous medium. International Journal of Biological Macromolecules, 184, 358-368.
[40] Yi, S. S., Lee, D. H., Sin, E., & Lee, Y. S. (2007). Chitosan-supported palladium (0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water. Tetrahedron Letters, 48(38), 6771-6775.
[41] Naghipour, A., & Fakhri, A. (2016). Heterogeneous Fe3O4@Xchitosan-Schiff base Pd nanocatalyst: Fabrication, characterization and application as highly efficient and magnetically-recoverable catalyst for Suzuki–Miyaura and Heck–Mizoroki C–C coupling reactions. Catalysis Communications, 73, 39-45.
[42] Baran, T., & Menteş, A. (2017). Construction of new biopolymer (chitosan)-based pincer-type Pd (II) complex and its catalytic application in Suzuki cross coupling reactions. Journal of Molecular Structure, 1134, 591-598.
[43] Baran, N. Y., Baran, T., & Menteş, A. (2018). Production of novel palladium nanocatalyst stabilized with sustainable chitosan/cellulose composite and its catalytic performance in Suzuki-Miyaura coupling reactions. Carbohydrate polymers, 181, 596-604.
[44] Baran, T., Yılmaz Baran, N., & Menteş, A. (2018). Sustainable chitosan/starch composite material for stabilization of palladium nanoparticles: Synthesis, characterization and investigation of catalytic behaviour of Pd@ chitosan/starch nanocomposite in Suzuki–Miyaura reaction. Applied Organometallic Chemistry, 32(2), e4075.
Applied Chemistry Today
Volume 19, Issue 70
May 2024
Pages 9-28

Files

Share

How to cite

Statistics