Synthesis, Characterization and Catalytic Study of a Novel Binuclear Paddle-wheel Palladium(II) Complex in the Mizoroki-Heck Reaction

Document Type : Research Paper

Authors

1 Department of Chemistry, Farhangian University, Tehran, Iran

2 Young Researchers and Elite Club, Islamshahr Branch, Islamic Azad University, Islamshahr, Iran

3 Cellular and Molecular Research Center, Research Institute for Cellular and Molecular Medicine, Urmia University of Medical Sciences, Urmia, Iran

4 Payame Noor University, Department of Chemistry, 19395-4697 Tehran, Iran

5 Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, Iran

Abstract

A new binuclear paddle-wheel palladium(II) complex of [Pd2(μ-mtzt)4]dmgH2 (1) has been prepared by the treatment of PdCl2 in acetonitrile with mixture of 1-methyl-1H-1,2,3,4-tetrazole-5-thiol (Hmtzt) and dimethylglyoxime (dmgH2) in methanol. Resulted complex was characterized by elemental analysis (CHNS), IR, UV–Vis absorption, 1H NMR spectroscopy and its structure was determined with single-crystal X-ray diffraction. Single crystal analysis reveals that this complex has binuclear structure in a paddle-wheel fashion with Pd-Pd distances of 2.808(2)Å. Also, in this binuclear complex, each palladium(II) ion has a slightly distorted square-pyramidal coordination geometry with the two nitrogen and two sulfur atoms in equatorial positions from four bridges mtzt- ligands and the second palladium subunit in axial position. Catalytic potentiality of complex 1 is also exhibited in the Mizoroki–Heck coupling reactions between a range of aryl halides and olefins. The catalyst shows very much efficient reactivity in the Mizoroki–Heck reactions giving high yield of the coupling products.

Keywords

References

[1] R.C. Olivares, O.J. Sandoval, S.H. Ortega, M.
Sanchez, R.A. Toscano, I. Haiduc, Heteroat. Chem. 6
(1995) 89.
[2] M. Taheriha, M. Ghadermazi, V. Amani, J. Mol.
Struct. 1107 (2016) 57.
[3] M.S. Majdolashrafi, A. Raissi Shabari, V. Amani,
Phosphorus Sulfur Silicon Relat. Elem. 192 (2017)
1188.
[4] S. Seyfi, R. Alizadeh, M. Darvish Ganji, V. Amani,
Spectrochimica Acta Part A: 190 (2018) 298.
[5] A.G. Zavaglia, I.D. Reva, L. Frija, M.L. Cristiano, R.
Fausto, J. Mol. Struct. 786 (2006) 182.
[6] H. Nöth, W. Beck, K. Burger, Eur. J. Inorg. Chem.
(1998) 93.
[7] S. Chen, Z. Kristallogr. NCS 227 (2012) 213.
[8] E.S. Lang, M. Dahmer, U. Abram, Acta Crystallogr.
C55 (1999) 854.
[9] Y.L. Wanga, Q. Shi, W.H. Bi, X. Li, R. Cao, Z.
Anorg. Allg. Chem. 632 (2006) 167.
[10] S. Ibáñez, D.N. Vrečo, F. Estevan, P. Hirva, M.
Sanaú, M.A. Úbeda, Dalton Trans. 43 (2014) 2961.
[11] Y. Yang, J. Gong, W. Zhang, H. Zhang, L. Zhang, Y.
Liu, H. Huang, H. Hu, Z. Kang, RSC. Adv. 2 (2012)
6414.
[12] M. Imran, A. Mix, B. Neumann, H.G. StammLer, U.
Monkowius, P. Bleckenwegner, N.W. Mitzel, Dalton
Trans. 43 (2014) 14737.
[13] U. Abram, J.R. Dilworth, Z. Anorg. Allg. Chem. 625
(1999) 609.
[14] M. Imran, A. Mix, B. Neumann, H.G. StammLer, U.
Monkowius, P. Bleckenwegner, N.W. Mitzel, Dalton
Trans. 44 (2015) 924.
[15] D. Dallinger, C.O. Kappe, Chem. Rev. 107 (2007)
2563.
[16] R.A. Sheldon, Green Chem. 7 (2005) 267.
[17] F. Diederich, P.J. Stang, Metal-Catalyzed Cross-
Coupling Reactions, Wiley-VCH, Weinheim,
Germany, 1998.
[18] M. Amini, D.B. Heydarloo, M. Rahimi, M.G. Kim, S.
Gautam, K.H. Chae, Mater. Res. Bull. 83 (2016) 179.
[19] L.S. Søbjerg, D. Gauthier, A.T. Lindhardt, M. Bunge,
K. Finster, R.L. Meyer, T. Skrydstrup, Green Chem.
11 (2009) 2041.
[20] M. Amini, M. Bagherzadeh, Z. Moradi-Shoeili, D.M.
Boghaei, RSC Adv. 2 (2012) 12091.
[21] S.M.S. Hussain, M.B. Ibrahim, A. Fazal, R. Suleiman,
M. Fettouhi, B.E. Ali, Polyhedron 70 (2014) 39.
[22] M. Bagherzadeh, M. Amini, A. Ellern, L.K. Woo,
Inorg. Chim. Acta 383 (2012) 46.
[23] G.M. Sheldrick, SADABS. Madison, WI, USA:
Bruker AXS, 1998.
[24] Bruker SMART and SAINT. Madison, WI, USA:
Bruker AXS Inc., 1998.
[25] G.M. Sheldrick. Acta Crystallogr. A64 (2008) 112.
[26] Mercury 141. Copyright Cambridge Crystallographic
Data Center. Cambridge, 2001-2005.
[27] S.S.A. Abidi, Y. Azim, A.K. Gupta, C.P. Pradeep, J.
Mol. Struct. 1150 (2017) 103.
[28] M.S. Majdolashrafi, A. Raissi Shabari, V. Amani,
Phosphorus Sulfur Silicon Relat. Elem. 193 (2018)
415.
[29] W. Clegg, C.D. Garner, M.H. Al-Samman, Inorg.
Chem. 2l (1982) 1897.
[30] K. Umakoshi, A. Ichimura, I. Kinoshita, S. Ooi, Inorg.
Chem. 29 (1990) 4005.
[31] A. Abedi, V. Amani, R. Boča, L. Dlháň, H.R.
Khavasi, N. Safari, Inorg. Chim. Acta 395 (2013) 58.
[32] S. Alvarez, Dalton Trans. 42 (2013) 8617.
Inorganic Chemistry Research
Volume 3, Issue 2
Autumn and Winter
2019
Pages 65-76

Files

History

  • Receive Date: 01 September 2019
  • Revise Date: 03 September 2019
  • Accept Date: 04 September 2019

Share

How to cite

Statistics