Synthesis of 1,3-diphenyl-2-propyn-1-ol derivatives in water catalyzed by silver ions immobilized on the magnetic cross-linked chitosan

الموضوعات : Iranian Journal of Catalysis

Fatemeh Rafiee ¹ (Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran)
Sahar Kermani ² (Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran)

تاريخ الإرسال : 28 الأربعاء , ذو الحجة, 1443 تاريخ التأكيد : 18 الإثنين , جمادى الأولى, 1444 تاريخ الإصدار : 07 السبت , جمادى الثانية, 1444

الکلمات المفتاحية: 1, Magnetic Chitosan, Chitosan supported catalysts, Silver catalyzed coupling reaction, 3-diphenyl-2-propyn-1-ol,

ملخص المقالة :

In this work, chitosan biopolymer was cross-linked by starch oxide through the covalent bond formation between amine groups of chitosan and aldehyde functional of oxidized starch. A magnetic bio-support was obtained due to the treatment of the produced hybrid biopolymer with iron oxide nanoparticles. As a result of exposing of silver nitrate salt to magnetic polymer, silver ions (Ag2O) and also Ag metal nanoparticles were deposited on this bio-support. The silver oxide was decorated on the magnetic chitosan biopolymer could catalyzed the cross-coupling reaction of substituted benzaldehydes with phenylacetylene in the presence of PPh3 (20 mol%) in water to achieve 1,3-diphenyl-2-propyn-1-ol derivatives in good yields at proper reaction times.

المصادر:

[1] P.G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2004 (2004) 4095-4105.

[2] R. Hua, T. A. Nizami, Org. Chem. 15 (2018) 198-207.

[3] S. Kotani, K. Kukita, K. Tanaka, T. Ichibakase, M. Nakajima, J. Org. Chem. 79 (2014) 4817-4825.

[4] L. Pu, Tetrahedron 59 (2003) 9873-9886.

[5] C. Chen, L. Hong, Z.-Q. Xu, L. Liu, R. Wang, Org. Lett. 8 (2006) 2277-2280.

[6] R. Takita, K. Yakura, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 127 (2005) 13760-13761.

[7] N. Sakai, R. Kanada, M. Hirasawa, T. Konakahara, Tetrahedron 61 (2005) 9298-9304.

[8] R. Takita, Y. Fukuta, R. Tsuji, T. Ohshima, M. Shibasaki, Org. Lett. 7 (2005) 1363-1366.

[9] C. Wei, C.J. Li, Green Chem. 4 (2002) 39–41.

[10] X. Yao, C.J. Li, Org. Lett. 7 (2005) 4395-4398.

[11] A. El Kadib, ChemsSusChem 8 (2015) 217-244.

[12] N.H. Azeman, N. Arsad, A.A.A. Bakar, Sensors (Basel) 20 (2020) 3924.

[13] M. Ottonelli, S. Zappia, A. Demartini, M.Alloisio, Nanomaterials (Basel). 10 (2020) 224.

[14] T.T.V. Phan, D.T. Phan, X.T. Cao, T.-C. Huynh, J. Oh, Nanomaterials 11 (2021) 273.

[15] A. Spoială, C.I. Ilie, D. Ficai, A. Ficai, E. Andronescu, Materials 14 (2021) 2091.

[16] P. Cazón, M. Vázquez, Applications of chitosan as food packaging materials. In: Crini G., Lichtfouse E. (eds) Sustainable Agriculture Reviews 36. Sustainable Agriculture Reviews, 36 (2019) 81-123.

[17] R. Parhi, Environ Chem. Lett. 18 (2020) 577–594.

[18] F. Rafiee, M. Rezaee, Int. J. Biol. Macromol. 179 (2021) 170-195.

[19] F. Rafiee, Curr. Org. Chem. 23 (2019) 390-408

[20] M. Kaloti, A. Kumar, ACS Omega. 3 (2018) 1529-1545.

[21] K. Hasan, I.A. Shehadi, N.D. Al-Bab, A. Elgamouz, Catalysts 9 (2019) 839.

[22] I. Sargin, Int. J. Biol. Macromol. 137 (2019) 576-582.

[23] R. Taheri-Ledari, S.S. Mirmohammadi, K. Valadi, A. Maleki, A.E. Shalan, RSC Adv. 10 (2020) 43670-43681.

[24] Y. Han, Y. Gao, X. Cao, M.M. Zangeneh, S. Liu, J. Li, Int. J. Biol. Macromol. 164 (2020) 2974-2986.

[25] B. Ramalingam, M.M.R. Khan, B. Mondal, A.B. Mandal, S.K. Das, ACS Sustainable Chem. Eng. 3 (2015) 2291-2302.

[26] M. Nikoorazm, P. Moradi, N. Noori, et al., J Iran. Chem. Soc., 18 (2021) 467–478.

[27] P. Moradi, M. Hajjami, New J. Chem., 45 (2021) 2981-2994.

[28] P. Moradi, M. Hajjami, RSC Adv., 11 (2021) 25867-25879.

[29] P. Moradi, M. Hajjami, RSC Adv., 12 (2022) 13523-13534.

[30] A. Ghorbani-Choghamarani, B.Tahmasbi, Z. Moradi, Appl Organometal Chem., 31 (2017) e3665.

[31] A. Ghorbani-Choghamarani, H. Rabiei, B. Tahmasbi, et al., Res Chem Intermed, 42 (2016) 5723–5737.

[32] B. Tahmasbi, A. Ghorbani-Choghamarani, New J. Chem., 43 (2019) 14485-14501.

[33] B. Atashkar, A. Rostami, H. Gholami, et al., Res Chem Intermed, 41 (2015) 3675–3681

[34] F. Rafiee, F. Rezaie Karder, React. Funct. Polym. 146, (2020) 104434.

[35] F. Rafiee, F. Rezaie Karder, Int. J. Biol. Macromol. 146 (2020) 1124-1132.

[36] F. Rafiee, S. Kermani, Iran J. Sci. Technol. Trans Sci. 45 (2021) 1631-1643.

[37] A. Ananth, Y.S. Mok, Nanomaterials 6 (2016) 42.

[38] T. Fang, D.M. Du, S.F. Lu, J. Xu, Org. Lett. 7 (2005) 2081–2084.

[39] Z.B. Li, L. Pu, Org. Lett. 6 (2004) 1065–1068.

[40] Z.C. Chen, X.P. Hui, C. Yin, L.N. Huang, P.F. Xu, X.X. Yu, S.Y. Cheng, J. Mol. Catal. A. Chem. 269 (2007) 179-182.

[41] L.N. Huang, X.P. Hui, Z.C. Chen, C. Yin, P.F. Xu, X.X. Yu, S.Y. Cheng, J. Mol. Catal. A. Chem. 275 (2007) 9-13.

[42] Y.F. Zhou, R. Wang, Z.Q. Xu, W.J. Yan, L. Liu, Y.F. Gao, C.S. Da, Tetrahedron Asymm., 15 (2004) 589-591.