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A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex as an efficient catalyst for oxidation of alcohols with tert-butyl hydroperoxide

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Abstract

A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex [PS–(QBIM)2Cu(II)] was synthesized by functionalization of chloromethylated polystyrene cross-linked with 6.5 % divinyl benzene with 2-(2′-quinolyl)benzimidazole and subsequent treatment with Cu(OAc)2 in methanol. The complex was characterized by physical, analytical and spectroscopic techniques. Electronic and ESR spectra, together with magnetic susceptibility measurements, indicated that the complex was paramagnetic with distorted octahedral geometry around the copper. The complex was found to be active toward oxidation of various alcohols including phenol, benzyl alcohol and cyclohexanol using 70 % aqueous tert-butyl hydroperoxide under mild conditions. Under the optimized reaction conditions, cyclohexanol gave 100 % conversion to cyclohexanone, benzyl alcohol gave 98 % yield of benzaldehyde and phenol gave 89 % yield of catechol and 4 % of hydroquinone. The complex was recycled five times without much loss in catalytic activity.

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References

  1. Anderson GL, Williams J, Hille R (1992) J Biol Chem 267:23674–23682

    CAS  Google Scholar 

  2. Suresh PS, Kumar A, Kumar R, Singh VP (2008) J Mol Graph Model 26:845–849

    Article  CAS  Google Scholar 

  3. Sato K, Kohzuma T, Dennison C (2003) J Am Chem Soc 125:2101–2112

    Article  CAS  Google Scholar 

  4. Boyer PD, Lardy H, Myrback K (eds) (1963) The enzymes, 2nd edn, vol 8. Academic Press, New York

  5. Kitajima N, Fujisawa K, Fujimoto C, Morooka Y, Hashimoto S, Kitagawa T, Toriumi K, Tatsumi K, Nakamura A (1992) J Am Chem Soc 114:1277–1291

    Article  CAS  Google Scholar 

  6. Solomon EI, Tuczek F, Root DE, Brown CA (1994) Chem Rev 94:827–856

    Article  CAS  Google Scholar 

  7. Caradonna In JP, King RB (1994) Encyclopedia of inorganic chemistry, vol 6, 2nd edn. Wiley, Chichester

    Google Scholar 

  8. Islam M, Hossain D, Mondal P, Tuhina K, Roy AS, Mondal S, Mobarak M (2011) Trans Met Chem 36:223–230

    Article  CAS  Google Scholar 

  9. Hwang JH, Abu-Omar MM (1999) Tetrahedron Lett 40:8313–8316

    Article  CAS  Google Scholar 

  10. Mohebbi S, Boghaei DM, Sarvestani AH, Salimi A (2005) Appl Catal A Gen 278:263–267

    Article  CAS  Google Scholar 

  11. Conte V, Di Furia F, Licini G (1997) Appl Catal A Gen 157:335–361

    Article  CAS  Google Scholar 

  12. Battistel E, Tassinari R, Fornaroli M, Bonoldi L (2003) J Mol Catal A: Chem 202:107–115

    Article  CAS  Google Scholar 

  13. Barbarini A, Maggi R, Muratori M, Sartori G, Sartorio R (2004) Tetrahedron Asymmetry 15:2467–2473

    Article  CAS  Google Scholar 

  14. Smith TS, Pecoraro VL (2002) Inorg Chem 41:6754–6760

    Article  CAS  Google Scholar 

  15. Hoppe E, Limberg C, Ziemer B (2006) Inorg Chem 45:8308–8317

    Article  CAS  Google Scholar 

  16. Figiel PJ, Sobczak JM, Ziolkowski JJ (2004) Chem Commun 2:244–245

    Article  Google Scholar 

  17. Rothernburg G, Feldberg L, Wiener H, Sasson Y (1998) J Chem Soc Perkin Trans 2:2429–2434

    Google Scholar 

  18. Striegler S (2006) Tetrahedron 62:9109–9114

    Article  CAS  Google Scholar 

  19. Ferguson G, Ajjou AN (2003) Tetrahedron Lett 44:9139–9142

    Article  CAS  Google Scholar 

  20. Muzart J (1992) Chem Rev 92:113–140

    Article  CAS  Google Scholar 

  21. Choudhary VR, Dumbre DK, Narkhede VS, Jana SK (2003) Cat Lett 86:229–233

    Article  CAS  Google Scholar 

  22. Castro IU, Sherrington DC, Fortuny A, Fabregat A, Stuber F, Font J, Bengoa C (2010) Catal Today 157:66–70

    Article  CAS  Google Scholar 

  23. Owsik IA, Kolarz BN, Jezierska J (2006) J Catal Lett 107:197–203

    Article  CAS  Google Scholar 

  24. Gupta KC, Sutar AK (2008) Polym Adv Technol 19:186–200

    Article  CAS  Google Scholar 

  25. Perrin DD, Armanego WCF, Perrin DR (1996) Purification of laboratory chemicals, I edn. Pergamon Press, New York

    Google Scholar 

  26. Haitt RR, Strachan WMJ (1963) J Org Chem 28:1893–1894

    Article  Google Scholar 

  27. Hisano T, Ichikawa M, Tsumoto K, Tasaki M (1982) Chem Pharm Bull 30:2996–3004

    Article  CAS  Google Scholar 

  28. Wang S, Cui Y, Tan R, Luo Q, Shi J, Wu Q (1994) Polyhedron 13:1661–1668

    Article  CAS  Google Scholar 

  29. Sathyanarayana DN (2001) Spectra of transition metal complexes—a survey, I edn. University press, India Ltd

    Google Scholar 

  30. Valodkar VB, Tembe GL, Ravindranathan M, Ram RN, Rama HS (2004) J Mol Catal A: Chem 208:21–32

    Article  CAS  Google Scholar 

  31. Sorokin AB, Mangematin S, Pergrale C (2002) J Mol Catal A: Chem 182–183:267–281

    Article  Google Scholar 

  32. Yiu Shek-Man, Man Wai-Lun, Lau Tai-Chu (2008) J Am Chem Soc 130:10821–10827

    Article  CAS  Google Scholar 

  33. Ishii Y, Iwahama T, Sakaguchi S, Nakayama K, Nishiyama Y (1996) J Org Chem 61:4520–4526

    Article  CAS  Google Scholar 

  34. Maurya MR, Arya A, Adao P, Pessoa JC (2008) Appl Catal A Gen 351:239–252

    Article  CAS  Google Scholar 

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Acknowledgments

Authors wish to thank UGC, New Delhi, India, for Major Research Project [F no. 39-741/2010(SR)]; Department of Chemistry, Bangalore University, Bangalore, for instrumentation facilities; and Thermax Ltd., for providing PS–DVB.

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  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, 560 001, India

    M. L. Shilpa & V. Gayathri

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  1. M. L. Shilpa
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  2. V. Gayathri
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Correspondence to V. Gayathri.

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Shilpa, M.L., Gayathri, V. A polymer-supported diacetatobis(2-quinolylbenzimidazole)copper(II) complex as an efficient catalyst for oxidation of alcohols with tert-butyl hydroperoxide. Transition Met Chem 38, 53–62 (2013). https://doi.org/10.1007/s11243-012-9660-x

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