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Preparation and Characterization of Pd/CuFe2O4 magnetic nanocatalyst and their application in Sonogashira cross-coupling reaction

Document Type : Research Paper

Authors

1 GUWAHATI COLLEGE

2 DIBRUGARH UNIVERSITY

Abstract
Herein we report the biogenic synthesis of Pd/CuFe2O4 magnetic nanocatalyst using Lantana camara flowers for the Sonogashira cross-coupling reaction. The as-prepared magnetic nanoparticles have been extensively characterized by powder X-ray diffraction (PXRD), SEM, EDX, TEM, HRTEM, ICP and BET surface area measurement techniques. The activity of different catalyst such as CuFe2O4, Pd/NiFe2O4 and Pd/Fe3O4 were investigated for Sonogashira cross-coupling reaction and it was observed that Pd/CuFe2O4 showed superior catalytic activity compared to the other catalyst systems. The use of non-toxic commercially available solvents, mild reaction conditions, easy preparation of the catalyst, high yield of the products and less reaction time are the advantages of the present protocol. The catalyst showed higher selectivity towards coupling of aryl halides with alkynes resulting in moderate to excellent isolated yields. The catalyst was easily separated with the help of an external magnet and reused upto 5th cycle without any significant loss in the catalytic activity and product yield.

Keywords

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[1]  C. Torborg and M.  Beller, Adv. Synth. Catal. 351, 3027-3043(2009) 
[2]  M.C. Kozlowski, B.J. Morgan and E.C. Linton, Chem. Soc. Rev. 38 3193-3207(2009)  
[3]  V. Francke, T. Mangel and K. Müllen, Macromolecules. 31 2447(1998) 
[4]  N. D. Cosford, L. Tehrani, J. Roppe, E. Schweiger, N. D. Smith, J. Anderson, L. Bristow, 
J. Brodkin, X. Jiang and I. Mc Donald, J. Med. Chem. 46,  204 (2003)  
[5]  M. M. Heravi, S. Sadjadi, Tetrahedron. 65, 7761 (2009) 
[6]  T. Hosseinnejad, M. Heravi, R. Firouzi, J. Mol. Model, 19, 951- 961 (2013)  
[7]  (a) L.H. Pignolet in: Plenum 1st
 Ed (New York 1983) (b) G.W. Parshall and S. Ittel in 
Homogeneous Catalysis: 2nd
 Ed (J. Wiley and Sons: New York 1992) p342. 
[8]  P. Siemsen, R.C. Livingston and F. Diederich, Angew. Chem. Int. Ed. 39, 2632–2657 
(2000) 
[9]  H. Kukula, S. Veit and A. Godt, Eur J Org Chem 277–286 (1999) 
[10]  J. Cheng, Y. Sun, F. Wang, M. Guo, J.H. Xu, Y. Pan, Z. Zhang, J Org Chem. 69, 5428-
5432 (2004) 
[11]  A. Arques, D. Aunon, P. Molina, Tetrahedron Lett. 45, 4337–4340 (2004) 
[12]  A. Mori, J. Kawashima, T. Shimada, M. Suguro, K. Hirabayashi, Y. Nishihara Org Lett. 
2, 2935–2937 (2000)  
[13]  D.A. Alonso, C. Najera, M.C. Pacheco, Tetrahedron Lett. 43, 9365–9368 (2002) 
[14]  D. Gelman, S.L. Buchwald, Angew Chem Int Ed. 42 5993–5996 (2003) 
[15]  I.P. Beletskaya, G.V. Latyshev, A.V. Tsvetkov, N.V. Lukashev, Tetrahedron Lett 44, 
5011–5013 (2003) 
[16]  L. Wang, P. Li, Y. Zhang, Chem. Commun. 514–515 (2004) 
[17]  A. Elangovan, Y.H. Wang, T.I. Ho, Org Lett 5,1841–1844 (2003)  
[18]  H.F. Chow, C.W. Wan, K.H. Low, Y.Y. Yeung, J Org Chem. 66 1910–1913 (2001) 
[19]  J. Cheng, Y. Sun, F. Wang, M. Guo, J.H. Xu, Y. Pan, Z. Zhang, J Org Chem. 695 428–
5432 (2004)  
[20]  A. Arques, D. Aunon, P. Molina, Tetrahedron Lett. 45 4337–4340 (2004)  
[21]  D.A. Alonso, C. Najera, M.C. Pacheco, Tetrahedron Lett. 43 9365–9368 (2002) 
[22]  D. Gelman, S.L. Buchwald, Angew Chem Int Ed. 42 5993–5996 (2003) 
[23]  G.W. Kabalka, L. Wang, V. Namboodiri, R.M. Pagni, Tetrahedron Lett, 41, 5151–5154 
(2000) 
[24]  Z.K. Ghezeli, M. Hekmati, H. Veisi, Appl. Organomet. Chem. 33, 4833 (2019) 
[25]  B. Atashkar, A. Rostami, M.A. Zolfigol, Appl Organomet Chem. 33, 4691 (2019)  
[26]  R. Chutia, B. Chetia, New J Chem. 44, 18199-18207 (2020) 
[27]  R. Chutia, B. Chetia, J of Coordination Chemistry. 73, 1925–1936 (2020) 
[28]  H. Firouzabadi, N. Iranpoor, M. Gholinejad, Tetrahedron. 65, 7079–7084 (2009) 
[29]  S. Martinez, M.M. Man, A. Vallribera, U. Schubert, A. Roig, E. Molins, New J Chem. 
30, 1093–1097 (2006) 
[30]  S.Abrahi Vahed ,F.Hemati Tirabadi, Int. J. New. Chem,9,393-404(2022) 
[31]  R. Chinchilla, C. Najera, Chem Soc Rev. 40, 5084–5121 (2011). 
[32]  A.M. Thomas, A. Sujatha, G. Anilkumar, RSC Adv. 4 21688-21698 (2014). 
[33]  A.K. Nezhad, F. Panahi, Green Chem. 13, 2408-2415 (2011). 
[34]  G. Hamasaka, D. Roy, A. Tazawa, Y. Uozumi, ACS Catal. 9, 11640-11646 (2019).  
[35]  S. Cheng, W. Wei, X. Zhang, H. Yu, M. Huang, M. Kazemnejadi, Green Chem. 22, 
2069-2076 (2020)  
[36]  K.L. Wilson, J. Murray, H.F. Sneddon, C. Jamieson, A.J.B. Watson, Synlett. 29, 2293-
2297 (2018)