Efficient oxidation of sulfides using a molybdenum(VI)–dioxo complex containing an benzimidazole ligand

Document Type: Articles

Authors

Department of Chemistry, Imam Hossein University, Tehran, Iran

Abstract

For the first time, dioxomolybdenum(VI) complex with the general formula [MoO2L2] containing a N-O bidentate ligands (HL=2-(o-aminophenyl)- benzimidazole) has been used for the oxidation of sulfides. Elemental analyses (carbon, hydrogen, nitrogen), FT-IR and Uv-Visble spectra and 1HNMR analysis agree well with the proposed stoicheiometry of the complex [MoO2L2].  A variety of sulfides were smoothly converted into the corresponding sulfoxide catalyzed by this molybdenum complex. The effect of the reaction conditions on the oxidation was studied by varying the amount of the catalyst, the amount of oxidant (UHP) and solvent type. Good yields with excellent selectivities were obtained in most cases.

Keywords


[1] M.J. Barber, P.J. Neame, J. Biol. Chem. 265 (1990) 20912-20915.
[2] O.A. Rajan, A. Chakravorty, Inorg. Chem. 20 (1981) 660-664.
[3] M.M. Abu-omar, A. Loaiza, N. Hontzeas, Chem. Rev. 105 (2005) 2227-2252.
[4] J. Topich, Inorg. Chem. 20 (1981) 3704-3707.
[5] E.I. Stiefel, Science 272 (1996) 1599-1600.
[6] R.H. Holm, Coord. Chem. Rev. 100 (1990) 183-221.
[7] J.T. Spence, Coord. Chem. Rev. 48 (1983) 59-82.
[8] G. Franz, R.A. Sheldon, in: B. Elvers, S. Hawkins, G. Shulz (Eds.), UIImann’s Encyclopedia of Industrial Chemistry, vol. A (18), 5th ed., VCH, Weinheim, 1991, pp. 261–311.
[9] J.T. Lutz, in: Kirk-Othmer, M. Grayson, D. Eckroth, G.J. Bushey, C.I. Eastman, A. Klingsberg, L. Spiro (Eds.), Encyclopedia of Chemical Technology, vol. 9, 3rd ed., Wiley, New York, 1980, pp. 251-266.
[10] W. Adam, C.R. Saha-Moller, P.A. Ganeshpure, Chem. Rev. 101 (2001) 3499-3548.
[11] J. Rudolph, K.L. Reddy, J.P. Chiang, K.B. Sharpless, J. Am. Chem. Soc. 119 (1997) 6189-6190.
[12] K. Sato, M. Adoki, M. Ogawa, T. Hashimoto, R. Noyori, J. Org. Chem. 61 (1996) 8310-8311.
[13] W. Adam, K.J. Roschmann, C.R. Saha-Moller, D. Seebach, J. Am. Chem. Soc. 124 (2002) 5068-5073.
[14] W. Zhang, J.L. Loebach, S.R. Wilson, E.N. Jacobsen, J. Am. Chem. Soc. 112 (1990) 2801-2803.
[15] D.E. de Vos, B.F. Sels, M. Reynaers, Y.V.S. Rao, P.A. Jacobsen, Tetrahedron Lett. 39 (1998) 3221-3224.
[16] P. Besgse, H. Veschambre, Tetrahedron 50 (1994) 8885-8927.
[17] R. Fazaeli, H. Aliyan, S. P. Foroushani, Z. Mohagheghian, Z. Heidari, Iran. J. Catal. 3 (2013) 129-137.
[18] R.A. Sheldon, J. Mol. Catal. 7 (1980) 107-126.
[19] L. Sumegi, A. Gerda, D. Gal, Oxid. Commun. 5 (1983) 25-32.
[20] F. Trifiro, P. Forzatti, S. Preite, J. Less-Common Met. 36 (1974) 319-328.
[21] J. Sobszak, J.J. Ziolkowski, Inorg. Chim. Acta 19 (1976) 15-18.
[22] M. Yamazaki, H. Endo, M. Tokoyama, Y. Kurusu, Bull. Chem. Soc. Jpn. 56 (1983) 3523-3524
[23] R.H. Holm, Chem. Rev. 87 (1987) 1401-1449.
[24] E.W. Harlan, J.M. Berg, R.H. Holm, J. Am. Chem. Soc. 108 (1986) 6992-7000.
[25] J.P. Caradonna, P.R. Reddy, R.H. Holm, J. Am. Chem. Soc. 110 (1988) 2139-2144.
[26] J.A. Craig, R.H. Holm, J. Am. Chem. Soc. 111 (1989) 2111-2115.
[27] N.R. Pramanik, S. Ghosh, T.K. Raychaudhuri, S. Ray, R.J. Butcher, S.S. Mandal, Polyhedron 23 (2004) 1595-1603.
[28] H.X. Liu, X.M. Zhang, X. Wang, Polyhedron 13 (1994) 441-444.
[29] J.A. Craig, E.W. Harlan, B.S. Synder, M.A. Whitener, R.H. Holm, Inorg. Chem. 28 (1989) 2082-2091.
[30] W. Boyd, J.T. Spence, Inorg. Chem. 21 (1982) 1602-1606.
[31] B.W. Hein, R.J. Alhem, J.J. Leavitt, J. Am. Chem. Soc. 79 (1957) 427-429.
[32] N. Bharti, Shailendra, M.T.G. Garza, D.E. Cruz-Vega, J. Castro-Garza, K. Saleem, F. Naqvi, M.R. Maurya, A. Azam, Bioorg. Med. Chem. Lett. 12 (2002) 869-871.
[33] X.Q. Buendı´a, A.E. Ruiz, A. Pena-Hueso, N.B. Behrens, R. Contreras, A.F. Parra, S. Berne`s, S.E. Castillo-Blum, Inorg. Chim. Acta 361 (2008) 2759-2767.
[34] O.A. Rajan, A. Chakravorty, Inorg. Chem. 20 (1981) 660-664.
[35] I. Sheikhshoaiea, A. Rezaeifardb, N. Monadi, S. Kaafi, Polyhedron 28 (2009) 733-738.
[36] N.Y. Jin, J. Coord. Chem. 65 (2012) 4008-4013.