Document Type : Original Research Article

Author

Department of Chemistry, Payame Noor University of Ilam, Iran

Abstract

Two polypyridyl copper(II) complexes, [Cu(phen)(phen-dione)Cl]Cl (1) and [Cu(bpy) (phen-dione)Cl]Cl (2), (where Phen =1,10-phenanthroline, bpy =2,2'-bipyridine and Phen-dione = 1,10-phenanthroline-5,6-dione), were used as efficient catalysts for the oxidation of benzyl alcohol to benzaldehyde. The effects of various parameters such as reaction temperature, reaction time, etc. were studied. The catalysts were stable at the operation conditions and recyclable. The conversion percentage for complex 1 was higher than the complex 2.

Graphical Abstract

Cataliticoxidation of benzyl alcohol by Cu(II) polypyridyl complexes

Keywords

Main Subjects

[1] M. Hudlicky, Oxidations in Organic Chemistry.,1990, ACS, Washington, U. S.A.
[2] R.C. Larock, Comprehensive Organic Transformations., 1999, VCH, New York, U. S. A.
[3] I.W.C.E. Arends, R.A. Sheldon, In Modern Oxidation Methods., 2010. Bäckvall, J.E, Ed, Wiley-VCH: Weinheim, Germany.
[4] W. Sun, Q. Sun, Acc. Chem. Res., 2019, 52, 2370-2381.
[5] X.-Q. Hao, J-J. Huang, T. Wang, J. Lv, J-F. Gong, M-P. Song, J. Org. Chem., 2014, 79, 9512-9530.
[6] X. Hu, Chimia., 2011, 65, 646–648
[7] D.A. Loginov, L.S. Shul'pina, D.V. Muratov, G.B. Shul'pin, Coord. Chem. Rev., 2019, 378, 1-31.
[8] R.R. Fernandes, M.V. Kirillova, J.A.L. da Silva, J.J.R. Fraústo da Silva, J.L. Pombeiro, Appl. Catal. A: Gen., 2009, 353, 107-112.
[9] A.A. Alshaheri, M.I.M. Tahir, M,B.A. Rahmana, T. Begum, T, A.Saleh., J. Mol. Liq., 2017, 240, 486-496.
[10] M.N. Kopylovich, A.J.L. Pombeiro, J. Mol. Catal. A: Chem., 2009, 305, 178-182.
[11] N. Xing, L.T. Xu, F.Y. Bai, H. Shan, Y.H. Xing, Z, Sh, Inorg, Chim. Acta., 2014, 409, 360-366.
[12] D.S. Nesterov, O.V. Nesterova, Catalysts., 2018, 8, 602-622.
[13] A. Nodzewska, A. Wadolowska, M, Watkinson, Coord. Chem. Rev., 2019, 382, 181-216.
[14] L.M.D.R.S. Martins, A.J.L. Pombeir, Inorg. Chim. Acta., 2017, 30, 390-397.
[15] R.L. Webster, Dalton. Trans, 2017, 46, 4483-4498.
[16] V.K. Bansal, R. Kumar, R. Prasad, S.P. Niraj, J. Mol. Catal. A: Chem., 2008, 284, 69-76.
[17] H.S. Abbo, S. Titinchi, J. Appl. Catal. A: Gen., 2009, 356, 167-171.
[18] R. Bikas, E. Shahmoradi, N. Noshiranzadeh, M. Emami, S. Reinoso, Inorg. Chim. Acta. ,2017, 466, 100-109. 
[19]R.F, Munhá, R.A. Zarkesh, A.F. Heyduk, Inorg. Chem., 2013, 52, 1124-11255.
[20] B. Louis, C. Detoni, N.M.F. Carvalho, C.D. Duarte, O.A.C. Antunes, Appl. Catal. A: Gen., 2009, 360, 218-225.
[21] T. Piou, T. Rovis, ACC. Chem. Res., 2018, 51, 170-180.
[22] A. Panja, Polyhedron, 2014, 25, 81-89.
[23] R.A. Sheldon, J.K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press: New York, U. S. A., 1981.
[24] J. García-Álvarez, J. Díez, J. Gimeno, C.M. Seifried, C. Vida, Inorg. Chem, 2013, 52, 5428-5437.
[25] R. Kağıt, O. Dayan, N, Özdemir, Polyhedron., 2016, 117, 504-512.
[26] M.M. Dell’Anna, M. Mali, P. Mastrorilli, P. Cotugno, A. Monopoli, J. Mole, Catal A: Chemi., 2014, 386, 114-119.
[27] H. Tavallaei, M. Jafarpour, F. Feizpour, A. Rezaeifard, A. Farrokhi, ACS Omega., 2019, 423, 601-3610.
[28] X. Liu, C. Manzur, N. Novoa, S. Celedón, D. Carrillo, J.R. Hamon, Coord. Chem. Rev., 2018, 357, 144-172.
[29] T. Suzuki, Chem. Rev., 2011, 111, 1825-1845.
[30] D. Das, P. Singh, O. Prakash, A.K. Singh, Inorg. Chem. Commun., 2010, 13, 1370-1373.
[31] K. Rajabimoghadam, Y. Darwish, U. Bashir, D. Pitman, S. Eichelberger, M.A. Siegler, M. Swart, I. Garcia-Bosch, J.  Am. Chem. Soc., 2018, 140, 48-61.
[32] J. Wu, Y. Liu, X. Ma, P. Liu, C. Gu, B. Dai, Appl.Organomet. Chem., 2016, 30, 577-580.
[33] C. Detoni, N.D.M.F. Carvalho, D.A.G. Aranda, B. Louis, O.A.C. Antunes,  Appl. Catal. A: Gen.,2009, 365, 281-286.
[34] R.J. Lassi, A.P.C.Ribeiro, M. Mendes, W. Rekik, G.A.O. Tiago, K.T. Mahmudov, H. Naïli, M.F.C. Guedes da Silva, A.J.L. Pombeir, Polyhedron., 2017, 17, 182-188.
[35] R. Bikas, F. Ajormal, M. Emami, N. Noshiranzadeh, A. Kozakiewicz, Inorg, Chim. Acta., 2018, 478, 77-87.
[36] H. Ünver, I. Kani, Polyhedron., 2017, 134, 257-262.
[37] R. Rahimi, E. Gholamrezapor, M. R. Naimi-jamal, Inorg. Chem. Commun., 2011, 14, 1561-1568.
[38] G. Zhang, L.L. Chengxiong Yang, E.L. James. G.A.L. Rheingold, Inorg. Chem. Commun., 2015, 51, 13-16.
[39] Z. Ma, L. Wei, E.C.B.A. Alegria, L.M.D.R.S. Martins, M. Fátima, C.G. da Silva, A.J.L. Pombeiro, Dalton Trans., 2014, 43, 4048-4058.
[40] H. Saravani, A.R. Rezvani, G. Mansouri, A.R. Salehi Rad, H.R. Khavasi, H. Hadadzadeh, Inorg. Chim. Acta.,2007, 360, 2829-2834.
[41] S. Al-Saeedi, L.H. Abdel-Rahman, A.M. Abu-Dief, S.M. Abdel-Fatah, T.M. Alotaibi, A.M. Alsalme, A. Nafady, Catalysts., 2018, 8, 452-464.