Skip to main content
SpringerLink
Log in

Copper doped K-birnessite as an efficient catalyst for the synthesis of 2-aryl benzimidazoles

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript

Abstract

In this study, an efficient and highly selective synthesis of 2-aryl benzimidazoles from the reaction of o-phenylenediamine and aromatic aldehydes in the presence of birnessite type copper doped manganese oxide (BCM) is reported. BCM was synthesized by the one-step hydrothermal method. Recycling of BCM up to five runs was investigated with appreciable yield and selectivity of the products. The best overall yields and selectivities were obtained in methanol. The crystal structure and thermal stability of BCM are characterized by using XRD, IR and thermal analysis techniques. The acid sites of BCM were investigated by IR using pyridine as a molecular probe. The improved catalytic activity observed in the BCM catalyst was associated to a high lattice oxygen mobility and availability due to the formation of Cu–O–Mn bridges.

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

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

Similar content being viewed by others

References

  1. Jadhav GR, Shaikh MU, Kale RP, Gill CH (2009) Chin Chem Lett 20:292–295

    Article  CAS  Google Scholar 

  2. Chari MA, Kenawy SE, Al-Deyab SS, Subba Reddy BV, Vinu A (2010) Tetrahedron Lett 51:5195–5199

    Article  CAS  Google Scholar 

  3. Shelkar R, Sarode S, Sarode J (2013) Tetrahedron Lett 54:6986–6990

    Article  CAS  Google Scholar 

  4. Hasan M, Munawar S, Khan N, Maqbool Z (1998) Turk J Chem 22:367–371

    CAS  Google Scholar 

  5. Alinezhad H, Salehian F, Biparva P (2012) Synth Commun 42:102–108

    Article  CAS  Google Scholar 

  6. Shingalapur RV, Hosamani KM (2010) Catal Lett 137:63–68

    Article  CAS  Google Scholar 

  7. Taha MAM, Chin J (2005) Chem Soc 52:137–140

    CAS  Google Scholar 

  8. Duan LP, Li Q, Wu NB, Xu DF, Zhang HB (2014) Chin Chem Lett 25:155–158

    Article  CAS  Google Scholar 

  9. Yuan J, Zhao Z, Zhu W, Li H, Qian X, Xu Y (2013) Tetrahedron 69:7026–7030

    Article  CAS  Google Scholar 

  10. Chari MA, Shobha D, Sasaki T (2011) Tetrahedron Lett 52:5575–5580

    Article  Google Scholar 

  11. Paul S, Basu B (2012) Tetrahedron Lett 32:4130–4133

    Article  Google Scholar 

  12. Deng QF, Ren TZ, Yuan ZY (2013) Reac Kinet Mech Cat 108:507–518

    Article  CAS  Google Scholar 

  13. D’alessandro O, Thomas HJ, Sambeth JE (2012) Reac Kinet Mech Cat 107:295–309

    Article  Google Scholar 

  14. Kunkalekar RK, Salker AV (2012) Reac Kinet Mech Cat 106:395–405

    Article  CAS  Google Scholar 

  15. Fakhreia A, Sagheer A, Zaki MI (2004) Microporous Mesoporous Mat 67:43–52

    Article  Google Scholar 

  16. Cai LN, Guo Y, Lu AH, Branton P, Li WC (2012) J Mol Catal A 360:35–41

    Article  CAS  Google Scholar 

  17. Kunkalekar RK, Salker AV (2013) Reac Kinet Mech Cat 108:173–182

    CAS  Google Scholar 

  18. Curia V, Sambeth J, Gambaro L (2012) Reac Kinet Mech Cat 106:165–176

    Article  CAS  Google Scholar 

  19. Jothiramalingam R, Viswanathan B, Varadarajan TK (2006) J Mol Catal A 252:49–55

    Article  CAS  Google Scholar 

  20. Zhı K, Lıu Q, Zhang Y, He S, He R (2010) J Fuel Chem Technol 38:445–451

    Article  Google Scholar 

  21. Kondrat SA, Davies TE, Zu Z, Boldrin P, Bartley JK, Carley AF, Taylor SH, Rosseinsky MJ, Hutchings GJ (2011) J Catal 281:279–289

    Article  CAS  Google Scholar 

  22. Li F, Zhang L, Evans DG, Duan X (2004) Colloids Surf A 244:169–177

    Article  CAS  Google Scholar 

  23. Patel A, Shukla P, Chen J, Rufford TE, Rudolph V, Zhu Z (2013) Catal Today 212:38–44

    Article  CAS  Google Scholar 

  24. Bandyopadhyay P, Sathe M, Prasad GK, Sharma P, Kaushik MP (2011) J Mol Catal 341:77–82

    Article  CAS  Google Scholar 

  25. Yu H, Zhang MS, Cui LR (2012) Chin Chem Lett 23:573–575

    Article  CAS  Google Scholar 

  26. Ghosh P, Mandal A (2011) Catal Commun 12:744–747

    Article  CAS  Google Scholar 

  27. Paul S, Basu B (2012) Tetrahedron Lett 53:4130–4133

    Article  CAS  Google Scholar 

  28. Salehi P, Dabiri M, Zolfigol MA, Otokesh S, Baghbanzadeh M (2006) Tetrahedron Lett 47:2557–2560

    Article  CAS  Google Scholar 

  29. Pramanik A, Roy R, Khan S, Ghatak A, Bhar S (2014) Tetrahedron Lett 55:1771–1777

    Article  CAS  Google Scholar 

  30. Varala R, Nasreen A, Enugala R, Adapa SR (2007) Tetrahedron Lett 48:69–72

    Article  CAS  Google Scholar 

  31. Mukhopadhyay C, Tapaswi K (2008) Catal Commun 9:2392–2394

    Article  CAS  Google Scholar 

  32. Trivedi R, De SK, Gibbs RA (2006) J Mol Catal 245:8–11

    Article  CAS  Google Scholar 

  33. Rekha M, Hamza A, Venugopal BR, Nagaraju N (2012) Chin J Catal 33:439–446

    Article  CAS  Google Scholar 

  34. Behbahani FK, Lotfi A (2013) Eur Chem Bull 2:694–697

    CAS  Google Scholar 

  35. Xiangming H, Huiqiang M, Yulu W (2007) Arkivoc (xiii):150–154

  36. Atkins AL, Shaw S, Peacock CL (2014) Geochim Cosmochim Acta 144:109–125

    Article  CAS  Google Scholar 

  37. Yin H, Liu F, Feng X, Liu M, Tan W, Qui G (2011) J Hazard Mater 196:318–326

    Article  CAS  Google Scholar 

  38. Eren E, Guney M, Eren B, Gumus H (2013) Appl Catal B 132–133:370–378

    Article  Google Scholar 

  39. Yang J, Wang B, Cao J, Han D, Feng B, Wei M, Fan L, Kou C, Liu Q, Wang T (2013) J Alloy Compd 574:240–245

    Article  CAS  Google Scholar 

  40. Li F, Wu J, Qin Q, Li Z, Huang X (2010) J Alloy Compd 492:339–346

    Article  CAS  Google Scholar 

  41. Cui M, Jang M, Na S, Lee S, Khim J (2013) J Environ Manag 115:235–240

    Article  CAS  Google Scholar 

  42. Liu L, Feng Q, Yanagisawa K, Bignall G, Hashida T (2002) J Mater Sci 37:1315–1320

    Article  CAS  Google Scholar 

  43. Malankar H, Umare SS, Singh K, Sharma M (2010) J Solid State Electrochem Room 14:71–82

    Article  CAS  Google Scholar 

  44. Gaillot AC, Lanson B, Drits VA (2005) Chem Mater 17:2959–2975

    Article  CAS  Google Scholar 

  45. Eren B, Erdogan G (2012) Reac Kinet Mech Cat 107:333–344

    Article  CAS  Google Scholar 

  46. Shimizu K, Higuchi T, Takasugi E, Hatamachi T, Kodama T, Satsuma A (2008) J Mol Catal A 284:89–96

    Article  CAS  Google Scholar 

  47. Figueiredo FCA, Jordão E, Landers R, Carvalho WA (2009) Appl Catal A 371:131–141

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We would like to thank reviewers for their remarks and corrections of the manuscript.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Arts, Bilecik Seyh Edebali University, 11210, Bilecik, Turkey

    Bilge Eren & Huseyin Gumus

Authors
  1. Bilge Eren
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Huseyin Gumus
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bilge Eren.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Eren, B., Gumus, H. Copper doped K-birnessite as an efficient catalyst for the synthesis of 2-aryl benzimidazoles. Reac Kinet Mech Cat 114, 571–582 (2015). https://doi.org/10.1007/s11144-014-0805-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-014-0805-0

Keywords

Search

Navigation