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Immobilized metalloporphyrins on 3-aminopropyl-functionalized silica support as heterogeneous catalysts for selective oxidation of primary and secondary alcohols

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Abstract

Iron(III), manganese(III), and cobalt(II) complexes of meso-tetrakis(p-chlorophenyl)porphyrin (Fe(TClPP)X, Mn(TClPP)X, and Co(TClPP)X, X = Cl or OAc) were immobilized onto 3-aminopropyl-functionalized silica (SF-3-APTS). SF-3-APTS acts as both axial base and support for immobilization of these metalloporphyrins. The obtained heterogeneous catalysts were characterized by Fourier transform infrared (FT-IR), UV–Vis, and inductively coupled plasma (ICP) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray (EDX), and thermogravimetric analysis (TGA) techniques. Their catalytic activity as biomimetic catalysts was investigated for the selective oxidation of primary and secondary benzylic alcohols to the corresponding carbonyl compounds with t-butylhydroperoxide as oxidant. SF-3-APTS–Fe(TClPP)Cl demonstrated higher catalytic activity than SF-3-APTS–Mn(TClPP)Cl and SF-3-APTS–Co(TClPP)OAc. The presence of electron-withdrawing substituents on benzylic alcohols enhances the rate of catalytic oxidation. SF-3-APTS–Fe(TClPP)Cl could be reused at least four times without significant loss of its catalytic activity.

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References

  1. Zondervan C, Hange R, Ben LF (1997) Chem Commun 419

  2. He J, Wu T, Tao J, Zhou X, Hu B, Han B (2008) Catal Commun 9:2239

    Article  CAS  Google Scholar 

  3. Rebelo SLH, Goncalves AR, Pereira MM (2006) J Mol Catal A Chem 256:321

    Article  CAS  Google Scholar 

  4. Liu ST, Reddy KV, Lai RY (2007) Tetrahedron 63:1821

    Article  CAS  Google Scholar 

  5. Nakagaki S, Halma M, Bail A (2005) J Colloid Interface Sci 281:417

    Article  CAS  Google Scholar 

  6. Feiters MC, Rowan AE (2000) Chem Soc Rev 29:375

    Article  CAS  Google Scholar 

  7. Baciocchi E, Belevedere S, Bietti M (1998) Tetrahedron Lett 39:4711

    Article  CAS  Google Scholar 

  8. Hong-Bing J, Qui-Lan Y, Xian-Tai Z, Li-Xia P, Le-Fu W (2007) Bioorg Med Chem Lett 17:6364

    Article  Google Scholar 

  9. Xian-Tai Z, Hong-Bing T, Zhao C, Jian-Chang X, Li-Xia P, Le-Fu W (2007) Bioorg Med Chem Lett 17:4650

    Article  Google Scholar 

  10. Moghaddam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Abbasi-Larki AA (2008) Appl Catal A Gen 349:177

    Article  Google Scholar 

  11. Rahimi R, Azhdari AR, Azizpoor-Fard M, Mirmohammadsadegh B, Khavasi HR (2009) Catal Commun 11:232

    Article  CAS  Google Scholar 

  12. Vinhado FS, Martins PR, Masson AP, Abreu DG, Vidoto EA, Nascimento OR, Imamoto YK (2002) J Mol Catal A Chem 188:141

    Article  CAS  Google Scholar 

  13. Ozaki S, Hamaguchi T, Tsuchida K, Kiamta Y (1989) J Chem Soc Perkin Trans 2:951

    Google Scholar 

  14. Huang JW, Huang WZ, Mei WJ, Liu J, Hu SG, Ti LN (2000) J Mol Catal A Chem 156:275

    Article  CAS  Google Scholar 

  15. Monsalves MS, Martins PR, Curi RB, Nascimento OR, Imamoto Y (2005) J Mol Catal A Chem 233:73

    Article  Google Scholar 

  16. Schiavon MA, Imamoto Y, Nascimento OR, Assis MD (2001) J Mol Catal A Chem 174:213

    Article  CAS  Google Scholar 

  17. Benedito FL, Nakagaki S, Saczk AA (2003) Appl Catal A Gen 250:1

    Article  CAS  Google Scholar 

  18. Gulino A, Mineo P, Scamporrino E, Vitalini D, Fragala I (2004) Chem Mater 16:1838

    Article  CAS  Google Scholar 

  19. Gracia-Sanchez MA, Tello SR, Sosa R, Campero A (2006) J Sol Gel Sci Technol 37:93

    Article  Google Scholar 

  20. Da-Silva MA, Oliverira DC, Papcidero AT, Mello C, Nassar EJ, Ciuffi KJ, Sacco HC (2003) J Sol Gel Sci Technol 26:329

    Article  CAS  Google Scholar 

  21. Machado AM, Wypych F, Drechsel SM, Nakagaki S (2002) J Colloid Interface Sci 254:158

    Article  CAS  Google Scholar 

  22. Levin PP, Costa SMB (2002) Int J Photoenergy 4:161

    Article  CAS  Google Scholar 

  23. Skorbot FC, Rosa ILV, Marques APA, Martins PR, Rocha J, Valente AA, Imamoto Y (2005) J Mol Catal A Chem 237:86

    Article  Google Scholar 

  24. Kalilur Rahiman A, Sreedaran S, Shanmunga Bharathi K, Narayanan V (2009) J Porous Mater 17:711

    Article  Google Scholar 

  25. Kishan MR, Rani VR, Murthy MRVS, Sitadevi P, Kulkarni SJ, Raghavan KV (2004) Appl Catal A Gen 223:263

    Google Scholar 

  26. Gao BJ, Wang RX (2009) J Appl Polym Sci 112:2764

    Article  CAS  Google Scholar 

  27. Cai H, Huang W (2009) J Sol Gel Sci Technol 50:430

    Article  CAS  Google Scholar 

  28. Dudas Z, Enache C, Fagadar-Cosma G, Armeanu I, Fagadar-Cosma E (2010) Mater Res Bull 45:1150

    Article  CAS  Google Scholar 

  29. Ghiaci M, Molaie F, Sedaghat ME, Dorostkar N (2010) Catal Commun 11:694

    Article  CAS  Google Scholar 

  30. Mokhtari J, Naimi-Jamal MR, Hamzeali H, Dekamin MG, Kaupp G (2009) ChemSusChem 2:248

    Article  CAS  Google Scholar 

  31. Meunier B (1992) Chem Rev 92:1411

    Article  CAS  Google Scholar 

  32. Oh NY, Suh Y, Park MJ, Seo MS, Kim J, Nam W (2005) Angew Chem Int Ed 117:4307

    Article  Google Scholar 

  33. Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J (1967) J Org Chem 32:476

    Article  CAS  Google Scholar 

  34. Adler AD, Longo FR, Kampas F, Kim J (1970) J Inorg Nucl Chem 32:2443

    Article  CAS  Google Scholar 

  35. Moghaddam M, Mirakhani V, Tangestaninejad S (2008) J Mol Catal A Chem 288:116

    Article  Google Scholar 

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Acknowledgments

We are grateful for the financial support from The Research Council of Iran University of Science and Technology (IUST), Iran.

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Authors and Affiliations

  1. Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran, 16846-13114, Iran

    Rahmatollah Rahimi, Seyyedeh Zahra Ghoreishi & Mohammad G. Dekamin

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  1. Rahmatollah Rahimi
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  2. Seyyedeh Zahra Ghoreishi
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  3. Mohammad G. Dekamin
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Correspondence to Rahmatollah Rahimi or Mohammad G. Dekamin.

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Rahimi, R., Ghoreishi, S.Z. & Dekamin, M.G. Immobilized metalloporphyrins on 3-aminopropyl-functionalized silica support as heterogeneous catalysts for selective oxidation of primary and secondary alcohols. Monatsh Chem 143, 1031–1038 (2012). https://doi.org/10.1007/s00706-011-0684-2

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  • DOI: https://doi.org/10.1007/s00706-011-0684-2

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