Ni(II) complexes immobilized on magnetic nanoparticles as an efficient semi-heterogeneous catalyst towards diastereoselective nitroaldol (Henry) reaction
Subject Areas :
seyed jamal tabatabaei
1
(دانشیار شیمی آلی، گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
پونه سیارنژاد
2
(کارشناسی ارشد شیمی آلی، گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
شیما اصغری
3
(کارشناسی ارشد شیمی آلی، گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
حمیده آقاحسینی
4
(پژوهشگر پسادکتری، گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
عاصمه مشهدی ملک زاده
5
(دکتری شیمی آلی، گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
علی رمضانی
6
(ریاست دانشکده علوم زیستی)
Keywords: Green synthesis, Henry reaction, Semi-heterogeneous catalyst, Ni(II) complex,
Abstract :
Using of magnetic and recyclable catalysts to promote selective C–C bond formation could help in the design of safer and ‘‘greener’’ chemical manufacturing process. This work describes the preparation of magneto Ni(II) complex (Fe3O4@PCA-Pic/NiII) as a novel semi-heterogeneous system and the evaluation of their potential catalytic activity towards the Henry (nitroaldol) reaction between nitroethane and a variety of aldehydes in aqueous medium. The morphology and structural feature of the catalyst was characterized using different microscopic and spectroscopic techniques such as FT-IR, UV-Vis, TGA, SEM, TEM, ICP, XRD, XPS and VSM. The Fe3O4@PCA-Pic/NiII represented perfect catalytic efficiency and good diastereoselectivity for the nitroaldol reaction. Other notable advantages of this work include high stability and reusability of the catalyst, green reaction conditions, ease of separation of products, and cost-effectiveness. Also, this catalyst can be recycled by applying an external magnetic field and reused up to ten runs without significant loss of activity.
[1] Goodman, G.T.; P. Roy. Soc. B-Biol. Sci. 185, 127-148, 1974.
[2] Höfer, R.; Bigorra, J.; Green Chem. 9, 203-212, 2007.
[3] Chaturvedi, S.; Dave, P.N.; Shah, N.K.; J. Saudi. Chem. Soc. 16, 307-325, 2012.
[4] Chang, J.S.; Hwang, J.S.; Park, S.E.; Res. Chem. Intermed. 29, 921-938, 2003.
[5] Fatemeh Rafiee, F.; Faezeh Rezaie karder, F.; Journal of Applied Research in Chemistry 13(2), 83-97, 2019.
[6] Anastas, P.T.; Zimmerman, J.B.; Green Chem. 21, 6545-6566, 2019.
[7] Kianmehr, E.; Roxana Fazli, R.; Gholamhosseyni, M.; Journal of Applied Research in Chemistry 12(3), 95-101, 2018.
[8] Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C.; Tetrahedron: Asymmetry 17, 3315-3326, 2006.
[9] Luzzio, F.A.; Tetrahedron 57(6), 915-945, 2001.
[10] Milner, S.E.; Moody, T.S.; Maguire, A.R.; Eur. J. Org. Chem. 2012(12), 3059-3067, 2012.
[11] Cwik, A.; Fuchs, A.; Hell, Z.; Clacens, J.M.; Tetrahedron 61, 4015-4021, 2005.
[12] M. Choudary, B.; Lakshmi Kantam, M.; Venkat Reddy, C.; Koteswara Rao, K.; Figueras, F.; Green Chemistry 1, 187-189, 1999.
[13] Doyle, A.G.; Jacobsen, E.N.; Chem. Rev. 107, 5713-5743, 2007.
[14] Yao, L.; Wei, Y.; Wang, P.; He, W.; Zhang, S.; Tetrahedron 68, 9119-9124, 2012.
[15] Ooi, T.; Doda, K.; Maruoka, K.; J. Am. Chem. Soc. 125, 2054-2055, 2003.
[16] Naïli, H.; Hajlaoui, F.; Mhiri, T.; Mac Leod, T.C.O.; Kopylovich, M.N.; Mahmudov, K.T.; Pombeiro, A.J.L.; Dalton. Trans. 42, 399-406, 2013.
[17] Christensen, C.; Juhl, K.; Hazell, R.G.; Jørgensen, K.A.; J. Org. Chem. 67, 4875-4881, 2002.
[18] Du, D.M.; Lu, S.F.; Fang, T.; Xu, J.; J. Org. Chem. 70, 3712-3715, 2005.
[19] Kopylovich, M.N.; Mizar, A.; Guedes da Silva, M.F.C.; Mac Leod, T.C.O.; Mahmudov, K.T.; Pombeiro, A.J.L.; Chem– A Eur. J. 19, 588-600, 2013.
[20] Lu, S.F.; Du, D.M.; Zhang, S.W.; Xu, J.; Tetrahedron: Asymmetry 15, 3433-3441, 2004.
[21] Tahir, N.; Wang, G.; Onyshchenko, I.; De Geyter, N.; Leus, K.; Morent, R.; Van Der Voort, P.; J. Catal. 375, 242-248, 2019.
[22] Köhn, U.; Schulz, M.; Görls, H.; Anders, E.; Tetrahedron: Asymmetry 16, 2125-2131, 2005.
[23] Kopylovich, M.N.; Mac Leod, T.C.O.; Mahmudov, K.T.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; Dalton. Trans. 40, 5352-5361, 2011.
[24] Palomo, C.; Oiarbide, M.; Laso, A.; Angew. Chem. Int. Edit. 44, 3881-3884, 2005.
[25] Karmakar, A.; Hazra, S.; Guedes da Silva, M.F.C.; Paul, A.; Pombeiro, A.J.L.; CrystEngComm. 18, 1337-1349, 2016.
[26] Taura, D.; Hioki, S.; Tanabe, J.; Ousaka, N.; Yashima, E.; ACS Catal. 6, 4685-4689, 2016.
[27] Wu, S.; Tang, J.; Han, J.; Mao, D.; Liu, X.; Gao, X.; Yu, J.; Wang, L.; Tetrahedron 70, 5986-5992, 2014.
[28] Chen, Z.; Yakura, K.; Matsunaga, S.; Shibasaki, M.; Org. Lett. 10, 3239-3242, 2008.
[29] Shepherd, N.E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M.; J. Am. Chem. Soc. 132, 3666-3667, 2010.
[30] Gao, W.; Xiang, B.; Meng, T.T.; Liu, F.; Qi, X.R.; Biomaterials 34, 4137-4149, 2013.
[31] Zhuang, R.; Liu, H.; Guo, J.; Dong, B.; Zhao, W.; Hu, Y.; Zhang, X.; Eur. Polym. J. 93, 358-367, 2017.
[32] Silva, T.F.S.; Rocha, B.G.M.; Guedes da Silva, M.F.C.; Martins, L.M.D.R.S.; Pombeiro, A.J.L.; New. J. Chem. 40, 528-537, 2016.
[33] Xavier, K.O.; Chacko, J.; Mohammed Yusuff, K.K.; Appl. Catal. A-Gen. 258, 251-259, 2004.
[34] Gupta, K.C.; Sutar, A.K.; Coordin. Chem. Rev. 252, 1420-1450, 2008.
[35] Mouri, S.; Chen, Z.; Matsunaga, S.; Shibasaki, M.; Chem. Commun. 5138-5140, 2009.
[36] Nkhili, N.L.; Rekik, W.; Mhiri, T.; Mahmudov, K.T.; Kopylovich, M.N.; Naïli, H.; Inorg. Chim. Acta. 412, 27-31, 2014.
[37] Allahresani, A.; J. Iran.Chem. Soc. 14, 1051-1057, 2017.
[38] Tabatabaei Rezaei, S.J.; Mashhadi Malekzadeh, A.; Poulaei, S.; Ramazani, A.; Khorramabadi, H.; Appl. Organomet. Chem. 32, e3975, 2018.
[39] Tabatabaei Rezaei, S.J.; Shamseddin, A.; Ramazani, A.; Mashhadi Malekzadeh, A.; Azimzadeh Asiabi, P.; Appl. Organomet. Chem. 31, e3707, 2017.
[40] Govan, J.; Gun; ko, K.Y.; Nanomaterials 4, 222-241, 2014.
[41] Nabid, M.R.; Bide, Y.; Tabatabaei Rezaei, S.J.; Appl. Catal. A-Gen. 406, 124-132, 2011.
[42] Shylesh, S.; Schünemann, V.; Thiel, W.R.; Angew. Chem. Int. Edit. 49, 3428-3459, 2010.
[43] Tabatabaei Rezaei, S.J.; Khorramabadi, H.; Hesami, A.; Ramazani, A.; Amani, V.; Ahmadi, R.; Ind. Eng. Chem. Res. 56, 12256-12266, 2017.
[44] Wang, D.; Astruc, D.; Chem. Rev. 114, 6949-6985, 2014.
[45] Mashhadi Malekzadeh, A.; Ramazani, A.; Tabatabaei Rezaei, S.J.; Niknejad, H.; J. Colloid. Interf. Sci. 490, 64-73, 2017.
[46] Dunetz, J.R.; Magano, J.; Weisenburger, G.A.; Org. Process. Res. Dev. 20, 140-177, 2016.
[47] Halcrow, M.A.; Chem. Soc. Rev. 42, 1784-1795, 2013.
[48] Karmakar, A.; Hazra, S.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; New. J. Chem. 38, 4837-4846, 2014.
[49] Sutradhar, M.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; Catal. Commun. 57, 103-106, 2014.
[50] Bulbule, V.J.; Deshpande, V.H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V.T.; Tetrahedron 55, 9325-9332, 1999.
[51] Nabid, M.R.; Bide, Y.; Aghaghafari, E.; Rezaei, S.J.T.; Catal. Lett. 144, 355-363, 2014.
[52] Adeli, M.; Mehdipour, E.; Bavadi, M.; J. Appl. Polym. Sci. 116, 2188-2196, 2010.
[53] Huang, X.; Li, L.; Liu, T.; Hao, N.; Liu, H.; Chen, D.; Tang, F.; ACS Nano. 5, 5390-5399, 2011.
[54] Coats, A.W.; Redfern, J.P.; Analyst 88, 906-924, 1963.
[55] Cullity, B.D.; Stock, S.R.; Elements of x-ray diffraction. Prentice Hall: Upper Saddle River, NJ, 2001.
[56] Li, Z.; Dong, H.; Zhang, Y.; Li, J.; Li, Y.; J. Colloid. Interf. Sci. 497, 43-49, 2017.
[57] Jung, Y.; Marcus, R.A.; J. Am. Chem. Soc. 129, 5492-5502, 2007.
[58] López, F.; Minnaard, A.J.; Feringa, B.L.; Accounts. Chem. Res. 40, 179-188, 2007.
[59] Sohtome, Y.; Hashimoto, Y.; Nagasawa, K.; Eur. J. Org. Chem. 2006, 2894-2897, 2006.
[1] Goodman, G.T.; P. Roy. Soc. B-Biol. Sci. 185, 127-148, 1974.
[2] Höfer, R.; Bigorra, J.; Green Chem. 9, 203-212, 2007.
[3] Chaturvedi, S.; Dave, P.N.; Shah, N.K.; J. Saudi. Chem. Soc. 16, 307-325, 2012.
[4] Chang, J.S.; Hwang, J.S.; Park, S.E.; Res. Chem. Intermed. 29, 921-938, 2003.
[5] Fatemeh Rafiee, F.; Faezeh Rezaie karder, F.; Journal of Applied Research in Chemistry 13(2), 83-97, 2019.
[6] Anastas, P.T.; Zimmerman, J.B.; Green Chem. 21, 6545-6566, 2019.
[7] Kianmehr, E.; Roxana Fazli, R.; Gholamhosseyni, M.; Journal of Applied Research in Chemistry 12(3), 95-101, 2018.
[8] Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C.; Tetrahedron: Asymmetry 17, 3315-3326, 2006.
[9] Luzzio, F.A.; Tetrahedron 57(6), 915-945, 2001.
[10] Milner, S.E.; Moody, T.S.; Maguire, A.R.; Eur. J. Org. Chem. 2012(12), 3059-3067, 2012.
[11] Cwik, A.; Fuchs, A.; Hell, Z.; Clacens, J.M.; Tetrahedron 61, 4015-4021, 2005.
[12] M. Choudary, B.; Lakshmi Kantam, M.; Venkat Reddy, C.; Koteswara Rao, K.; Figueras, F.; Green Chemistry 1, 187-189, 1999.
[13] Doyle, A.G.; Jacobsen, E.N.; Chem. Rev. 107, 5713-5743, 2007.
[14] Yao, L.; Wei, Y.; Wang, P.; He, W.; Zhang, S.; Tetrahedron 68, 9119-9124, 2012.
[15] Ooi, T.; Doda, K.; Maruoka, K.; J. Am. Chem. Soc. 125, 2054-2055, 2003.
[16] Naïli, H.; Hajlaoui, F.; Mhiri, T.; Mac Leod, T.C.O.; Kopylovich, M.N.; Mahmudov, K.T.; Pombeiro, A.J.L.; Dalton. Trans. 42, 399-406, 2013.
[17] Christensen, C.; Juhl, K.; Hazell, R.G.; Jørgensen, K.A.; J. Org. Chem. 67, 4875-4881, 2002.
[18] Du, D.M.; Lu, S.F.; Fang, T.; Xu, J.; J. Org. Chem. 70, 3712-3715, 2005.
[19] Kopylovich, M.N.; Mizar, A.; Guedes da Silva, M.F.C.; Mac Leod, T.C.O.; Mahmudov, K.T.; Pombeiro, A.J.L.; Chem– A Eur. J. 19, 588-600, 2013.
[20] Lu, S.F.; Du, D.M.; Zhang, S.W.; Xu, J.; Tetrahedron: Asymmetry 15, 3433-3441, 2004.
[21] Tahir, N.; Wang, G.; Onyshchenko, I.; De Geyter, N.; Leus, K.; Morent, R.; Van Der Voort, P.; J. Catal. 375, 242-248, 2019.
[22] Köhn, U.; Schulz, M.; Görls, H.; Anders, E.; Tetrahedron: Asymmetry 16, 2125-2131, 2005.
[23] Kopylovich, M.N.; Mac Leod, T.C.O.; Mahmudov, K.T.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; Dalton. Trans. 40, 5352-5361, 2011.
[24] Palomo, C.; Oiarbide, M.; Laso, A.; Angew. Chem. Int. Edit. 44, 3881-3884, 2005.
[25] Karmakar, A.; Hazra, S.; Guedes da Silva, M.F.C.; Paul, A.; Pombeiro, A.J.L.; CrystEngComm. 18, 1337-1349, 2016.
[26] Taura, D.; Hioki, S.; Tanabe, J.; Ousaka, N.; Yashima, E.; ACS Catal. 6, 4685-4689, 2016.
[27] Wu, S.; Tang, J.; Han, J.; Mao, D.; Liu, X.; Gao, X.; Yu, J.; Wang, L.; Tetrahedron 70, 5986-5992, 2014.
[28] Chen, Z.; Yakura, K.; Matsunaga, S.; Shibasaki, M.; Org. Lett. 10, 3239-3242, 2008.
[29] Shepherd, N.E.; Tanabe, H.; Xu, Y.; Matsunaga, S.; Shibasaki, M.; J. Am. Chem. Soc. 132, 3666-3667, 2010.
[30] Gao, W.; Xiang, B.; Meng, T.T.; Liu, F.; Qi, X.R.; Biomaterials 34, 4137-4149, 2013.
[31] Zhuang, R.; Liu, H.; Guo, J.; Dong, B.; Zhao, W.; Hu, Y.; Zhang, X.; Eur. Polym. J. 93, 358-367, 2017.
[32] Silva, T.F.S.; Rocha, B.G.M.; Guedes da Silva, M.F.C.; Martins, L.M.D.R.S.; Pombeiro, A.J.L.; New. J. Chem. 40, 528-537, 2016.
[33] Xavier, K.O.; Chacko, J.; Mohammed Yusuff, K.K.; Appl. Catal. A-Gen. 258, 251-259, 2004.
[34] Gupta, K.C.; Sutar, A.K.; Coordin. Chem. Rev. 252, 1420-1450, 2008.
[35] Mouri, S.; Chen, Z.; Matsunaga, S.; Shibasaki, M.; Chem. Commun. 5138-5140, 2009.
[36] Nkhili, N.L.; Rekik, W.; Mhiri, T.; Mahmudov, K.T.; Kopylovich, M.N.; Naïli, H.; Inorg. Chim. Acta. 412, 27-31, 2014.
[37] Allahresani, A.; J. Iran.Chem. Soc. 14, 1051-1057, 2017.
[38] Tabatabaei Rezaei, S.J.; Mashhadi Malekzadeh, A.; Poulaei, S.; Ramazani, A.; Khorramabadi, H.; Appl. Organomet. Chem. 32, e3975, 2018.
[39] Tabatabaei Rezaei, S.J.; Shamseddin, A.; Ramazani, A.; Mashhadi Malekzadeh, A.; Azimzadeh Asiabi, P.; Appl. Organomet. Chem. 31, e3707, 2017.
[40] Govan, J.; Gun; ko, K.Y.; Nanomaterials 4, 222-241, 2014.
[41] Nabid, M.R.; Bide, Y.; Tabatabaei Rezaei, S.J.; Appl. Catal. A-Gen. 406, 124-132, 2011.
[42] Shylesh, S.; Schünemann, V.; Thiel, W.R.; Angew. Chem. Int. Edit. 49, 3428-3459, 2010.
[43] Tabatabaei Rezaei, S.J.; Khorramabadi, H.; Hesami, A.; Ramazani, A.; Amani, V.; Ahmadi, R.; Ind. Eng. Chem. Res. 56, 12256-12266, 2017.
[44] Wang, D.; Astruc, D.; Chem. Rev. 114, 6949-6985, 2014.
[45] Mashhadi Malekzadeh, A.; Ramazani, A.; Tabatabaei Rezaei, S.J.; Niknejad, H.; J. Colloid. Interf. Sci. 490, 64-73, 2017.
[46] Dunetz, J.R.; Magano, J.; Weisenburger, G.A.; Org. Process. Res. Dev. 20, 140-177, 2016.
[47] Halcrow, M.A.; Chem. Soc. Rev. 42, 1784-1795, 2013.
[48] Karmakar, A.; Hazra, S.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; New. J. Chem. 38, 4837-4846, 2014.
[49] Sutradhar, M.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.; Catal. Commun. 57, 103-106, 2014.
[50] Bulbule, V.J.; Deshpande, V.H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V.T.; Tetrahedron 55, 9325-9332, 1999.
[51] Nabid, M.R.; Bide, Y.; Aghaghafari, E.; Rezaei, S.J.T.; Catal. Lett. 144, 355-363, 2014.
[52] Adeli, M.; Mehdipour, E.; Bavadi, M.; J. Appl. Polym. Sci. 116, 2188-2196, 2010.
[53] Huang, X.; Li, L.; Liu, T.; Hao, N.; Liu, H.; Chen, D.; Tang, F.; ACS Nano. 5, 5390-5399, 2011.
[54] Coats, A.W.; Redfern, J.P.; Analyst 88, 906-924, 1963.
[55] Cullity, B.D.; Stock, S.R.; Elements of x-ray diffraction. Prentice Hall: Upper Saddle River, NJ, 2001.
[56] Li, Z.; Dong, H.; Zhang, Y.; Li, J.; Li, Y.; J. Colloid. Interf. Sci. 497, 43-49, 2017.
[57] Jung, Y.; Marcus, R.A.; J. Am. Chem. Soc. 129, 5492-5502, 2007.
[58] López, F.; Minnaard, A.J.; Feringa, B.L.; Accounts. Chem. Res. 40, 179-188, 2007.
[59] Sohtome, Y.; Hashimoto, Y.; Nagasawa, K.; Eur. J. Org. Chem. 2006, 2894-2897, 2006.
