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Oxidative Dimerization of o-Aminophenol by Heterogeneous Mesoporous Material Modified with Biomimetic Salen-Type Copper(II) Complex

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Abstract

Copper(II) N,N′-bis[4-(N,N-diethylamino)salicylidene]ethylenediamine (CAS) complex, which has the metal–ligand coordination “CuN2O2” that mimics the galactose enzyme active site, was synthesised and incorporated onto the organo-modified MCM-48. The supported CAS catalyst successfully catalysed the conversion of o-aminophenol to 2-amino-3H-phenoxazon-3-one in the presence of aqueous peroxide as oxidant. The catalytic performance of the CAS supported on organo-modified MCM-48 was found highly affected by the temperature, the type of aqueous peroxide and reaction solvent used.

Graphical Abstract

A salen-type copper complex of N2O2 donor ligand was synthesised and incorporated onto the modified MCM-48. The corresponding supported catalysts are active in the oxidation of o-aminophenol to 2-amino-3H-phenoxazin-3-one in the presence of peroxide as an oxidant.

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References

  1. Mukherjee M, Ray AR (2007) J Mol Catal A 266:207

    Article  CAS  Google Scholar 

  2. Dores Assis M, Mole AJB, Serra OA, Iamamoto Y (1995) J Mol Catal A 97:41

    Article  Google Scholar 

  3. Mansuy D (1993) Coord Chem Rev 125:129

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. Gunter MJ, Turner T (1991) Coord Chem Rev 108:115

    Article  CAS  Google Scholar 

  6. Ricoux R, Raffy Q, Mahy JP (2007) C R Chimie 10:684

    Article  CAS  Google Scholar 

  7. Lu Y, Berry M, Pfister TD (2001) Chem Rev 101:3047

    Article  CAS  Google Scholar 

  8. Mirkhani V, Moghadam M, Tangestaninejad S, Bahramian B, Mallekpoor-Shalamzari A (2007) Appl Catal A Gen 321:49

    Article  CAS  Google Scholar 

  9. Prasetyoko D, Fansuri H, Ramli Z, Endud S, Nur H (2009) Catal Lett 128:177

    Article  CAS  Google Scholar 

  10. Sakthivel A, Sun W, Raudaschl-Sieber G, Chiang AST, Hanzlik M, Kühn FE (2006) Catal Commun 7:302

    Article  CAS  Google Scholar 

  11. O’Connor KJ, Wey SJ, Burrows CJ (1992) Tetrahedron Lett 33:1001

    Article  Google Scholar 

  12. Kim GJ, Chin JH (1999) Catal Lett 63:83

    Article  CAS  Google Scholar 

  13. Bhadbhade MM, Srinivas D (1993) Inorg Chem 32:6122

    Article  CAS  Google Scholar 

  14. Lauffer RB, Heistand RH II, Heistand RH II, Que L Jr (1983) Inorg Chem 22:50

    Article  CAS  Google Scholar 

  15. Çevik U, Değirmencioğlu I, Ertuğral B, Apaydin G, Baltaş H (2005) Eur Phys J D 36:29

    Article  Google Scholar 

  16. Venkataramanan NS, Kuppuraj G, Rajagopal S (2005) Coord Chem Rev 249:1249

    Article  CAS  Google Scholar 

  17. Budagumpi S, Johnson RP, Suh H, Ha C-S, Kim I (2011) Catal Lett 141:1219

    Article  CAS  Google Scholar 

  18. Horváth T, Kaizer J, Speier G (2004) J Mol Catal A 215:9

    Article  Google Scholar 

  19. Solomon EI, Baldwin MJ, Lowery MD (1992) Chem Rev 92:521

    Article  CAS  Google Scholar 

  20. Koval IA, Gamez P, Reedijk J (2008) In: Pignataro B (ed) Tomorrow’s chemistry today: concepts in nanoscience, organic materials and environmental chemistry. Wiley-VCH, Weinheim, p 101

    Google Scholar 

  21. Jacob CR, Varkey SP, Ratnasamy P (1998) Appl Catal 168:353

    Article  CAS  Google Scholar 

  22. Jazdzewski BA, Tolman WB (2000) Coord Chem Rev 633:200–202

    Google Scholar 

  23. Simándi TM, Simándi LI, Győr M, Rockenbauer A, Gömöry A (2004) J Chem Soc Dalton Trans 7:1056

    Google Scholar 

  24. Hassanein M, Abdo M, Gerges S, El-Khalafy S (2008) J Mol Catal A 287:53

    Article  CAS  Google Scholar 

  25. Szihyártó IC, Simándi TM, Simándi LI, Korecz L, Nagy N (2006) J Mol Catal A 251:270

    Article  Google Scholar 

  26. Hasegawa KI, Ueno Y (1985) Bull Chem Soc Jpn 58:2832

    Article  CAS  Google Scholar 

  27. Tomoda A, Arai S, Ishida R, Shimamoto T, Ohyashiki K (2001) Bioorg Med Chem Lett 11:1057

    Article  CAS  Google Scholar 

  28. Maurya MR, Sikarwar S, Joseph T, Halligudi SB (2005) J Mol Catal A 236:132

    Article  CAS  Google Scholar 

  29. El-Safty SA, Evans J, El-Seikh MY, Zaki AB (2002) Colloid Surf A 203:217

    Article  CAS  Google Scholar 

  30. Taguchi A, Schüth F (2005) Micropor Mesopor Mater 77:1

    Article  CAS  Google Scholar 

  31. Nur H, Hamid H, Endud S, Hamdan H, Ramli Z (2006) Mater Chem Phys 96:337

    Article  CAS  Google Scholar 

  32. Endud S, Wong KL (2007) Micorpor Mesopor Mater 101:256

    Article  CAS  Google Scholar 

  33. Gents MB, Nielsen ST, Mortensen AG, Christophersen C, Fomsgaard IS (2005) Chemosphere 61:74

    Article  CAS  Google Scholar 

  34. Gagliardo RW, Chilton WS (1992) J Chem Ecol 18:1683

    Article  CAS  Google Scholar 

  35. Chaube VD, Shylesh S, Singh AP (2005) J Mol Catal A 241:79

    Article  CAS  Google Scholar 

  36. Bahramian B, Mirkhani V, Moghadam M, Tangestaninejad S (2006) Catal Commun 7:289

    Article  CAS  Google Scholar 

  37. Kozlov A, Asakura K, Iwasawa Y (1998) Micropor Mesopor Mater 21:571

    Article  CAS  Google Scholar 

  38. El-Khalafy SH, Hassanein M (2012) J Mol Catal A 148:363–364

    Google Scholar 

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Acknowledgments

S. Endud thanks Universiti Teknologi Malaysia (UTM) for the Research University grant Q.J.130000.7113.02H23 and MOSTI for the National Nanotechnology Directorate Top-Down Grant R.J130000.7926.4H007. Authors thank the Ibnu Sina Institute for Fundamental Science Studies, UTM for research facilities. S. Budagumpi thanks UTM for a post-doctoral research fellowship.

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Correspondence to Salasiah Endud.

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Chin, TK., Endud, S., Jamil, S. et al. Oxidative Dimerization of o-Aminophenol by Heterogeneous Mesoporous Material Modified with Biomimetic Salen-Type Copper(II) Complex. Catal Lett 143, 282–288 (2013). https://doi.org/10.1007/s10562-012-0959-1

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