Skip to main content
SpringerLink
Log in

Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

Chloromethylated polystyrene beads cross-linked with 6.5 % divinylbenzene were functionalized with 2-(2′-pyridyl) benzimidazole (PBIMH) and on subsequent treatment with Cu(OAc)2 in methanol gave a polymer-supported diacetatobis(2-pyridylbenzimidazole)copper(II) complex [PS-(PBIM)2Cu(II)], which was characterized by physicochemical techniques. The supported complex showed excellent catalytic activity toward the oxidation of industrially important organic compounds such as phenol, benzyl alcohol, cyclohexanol, styrene, and ethylbenzene. An effective catalytic protocol was developed by varying reaction parameters such as the catalyst and substrate concentrations, reaction time, temperature, and substrate-to-oxidant ratio to obtain maximum selectivity with high yields of products. Possible reaction mechanisms were worked out. The catalyst could be recycled five times without any metal leaching or much loss in activity. This catalyst is truly heterogeneous and allows for easy work up, as well as recyclability and excellent product yields under mild conditions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Gayathri V, Leelamani EG, Nanje Gowda NM, Narayana Reddy GK (1999) Polyhedron 18:2351–2360

    Article  CAS  Google Scholar 

  2. Gayathri V, Leelamani EG, Nanje Gowda NM, Narayana Reddy GK (2000) Trans Met Chem 25:450–455

    Article  CAS  Google Scholar 

  3. Roopashree B, Gayathri V, Mukund H (2012) J Coord Chem 65:1354–1370

    Article  CAS  Google Scholar 

  4. Chandrashekar N, Gayathri V, Nanje Gowda NM (2009) Mag Reson Chem 47:666–673

    Article  Google Scholar 

  5. Chandrashekar N, Gayathri V, Nanje Gowda NM (2010) Polyhedron 29:288–295

    Article  Google Scholar 

  6. Raman SS, Nampoori VPN, Vallabhan CPG (1999) J Mater Sci Lett 18:1887–1889

    Article  CAS  Google Scholar 

  7. Perez Y, Ballesteros R, Fajardo M, Sierra I, del Hierro I (2012) J Mol Catal A Chem 352:45–56

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  9. Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X (2011) Org Lett 13:2274–2277

    Article  CAS  Google Scholar 

  10. Yi CS, Kwon KH, Lee DW (2009) Org Lett 11:1567–1569

    Article  CAS  Google Scholar 

  11. Liu Y, Tsunoyama H, Akita T, Tsukuda T (2010) Chem Commun 46:550–552

    Google Scholar 

  12. Lurain AE, Maestri A, Kelli AR, Carroll PJ, Walsh PJ (2004) J Am Chem Soc 126:13622–13623

    Article  Google Scholar 

  13. Maurya MR, Kumar M, Sikarwar S (2006) React Funct Polym 66:808–818

    Article  CAS  Google Scholar 

  14. Alexander S, Udayakumar V, Nagaraju N, Gayathri V (2010) Trans Met Chem 35:247–251

    Article  CAS  Google Scholar 

  15. Udayakumar V, Alexander S, Gayathri V, Shivakumaraiah, Patil KR, Viswanathan B (2010) J Mol Catal A Chem 317:111–117

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  Google Scholar 

  18. Hein IW, Arhum RI, Liquitt JJ (1957) J Am Chem Soc 79:427–429

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. Shilpa ML, Gayathri V (2013) Trans Met Chem 38:53–62

    Article  CAS  Google Scholar 

  25. Islam SM, Mondal P, Mukherjee S, Roy AS, Bhaumik A (2011) Polym Adv Technol 22:933–941

    Article  CAS  Google Scholar 

  26. Islam SM, Mondal P, Tuhina K, Roy AS, Hossain D, Mondal S (2010) Trans Met Chem 35:891–901

    Article  CAS  Google Scholar 

  27. Maurya MR, Kumar M, Kumar U (2007) J Mol Catal A Chem 273:133–143

    Article  CAS  Google Scholar 

  28. Sharma S, Sinha S, Chand S (2012) Ind Eng Chem Res 51:8709–9198

    Article  Google Scholar 

  29. Islam SM, Mondal P, Mondal S, Mukherjee S, Roy AS, Mubarak M, Paul M (2010) J Inorg Organomet Polym 20:87–96

    Article  CAS  Google Scholar 

  30. Gupta KC, Sutar AK (2008) J Mol Catal A Chem 280:173–185

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. Maurya MR, Sikarwar S, Joseph T, Manikandan P, Halligudi SB (2005) Reac Funct Polym 63:71–83

    Article  CAS  Google Scholar 

  33. Wang Y, Chang Y, Wang R, Zha F (2000) J Mol Cat A Chem 159:31–35

    Article  CAS  Google Scholar 

Download references

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; Thermax Ltd., is gratefully acknowledged for providing PS-DVB .

Author information

Authors and Affiliations

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

    M. L. Shilpa & V. Gayathri

Authors
  1. M. L. Shilpa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Gayathri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Gayathri.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 504 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shilpa, M.L., Gayathri, V. Liquid-phase catalytic oxidation of organic substrates by a recyclable polymer-supported copper(II) complex. Transition Met Chem 38, 705–713 (2013). https://doi.org/10.1007/s11243-013-9740-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-013-9740-6

Keywords

Search

Navigation