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An efficient polymer-supported copper(II) catalyst for the N-arylation reaction of N(H)-heterocycles with aryl halides as well as arylboronic acids

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Abstract

Immobilization of copper onto polystyrene provided a polymer-supported copper(II) catalyst, which was effective in cross-coupling reactions between N-containing substrates and arylboronic acids using methanol as a solvent in air under base-free conditions. This catalyst was also effective in N-arylation of imidazole with aryl halides in DMSO using K2CO3 as a base under nitrogen atmosphere. The catalyst was characterized by physico-chemical and spectroscopic techniques. The product N-arylimidazoles and N-arylbenzimidazoles were isolated in good to excellent yields. This copper catalyst was air stable and could be recycled with minimal loss of activity.

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References

  1. Beletskaya IP, Cheprakov AV (2004) Coor Chem Rev 248:2337–2364

    Article  CAS  Google Scholar 

  2. Ullmann F, Ber D (1903) Chem Ges 40:2382

    Article  Google Scholar 

  3. Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400

    Article  CAS  Google Scholar 

  4. Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL (1998) Acc Chem Res 31:805

    Article  CAS  Google Scholar 

  5. Lewis JC, Bergman RG, Ellman JA (2008) Acc Chem Res 41:1013

    Article  CAS  Google Scholar 

  6. Ohmori J, Shimizu-Sasamata M, Okada M, Sakamoto SJ (1996) J Med Chem 39:3971

    Google Scholar 

  7. Pavik WJJW, Connors RE, Burns DS, Kurzweil EM (1993) J Med Chem 115:7645

    Google Scholar 

  8. Lam PYS, Deudon S, Averill KM, Li R, He MY, Deshong P, Clark CG (2000) J Am Chem Soc 122:7600

    Article  CAS  Google Scholar 

  9. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359

    Article  CAS  Google Scholar 

  10. Zhang H, Cai Q, Ma D (2005) J Org Chem 70:5164

    Article  CAS  Google Scholar 

  11. Antilla JC, Baskin JM, Barder TE, Buchwald SL (2004) J Org Chem 69:5578

    Article  CAS  Google Scholar 

  12. Kwong FY, Klapars A, Buchwald SL (2002) Org Lett 4:581

    Article  CAS  Google Scholar 

  13. Lam PYS, Clark CG, Saubern S, Adams J, Averill KM, Chan DMT, Combs A (2000) Synlett :674

  14. Lan JB, Chen L, Yu XQ, You JS, Xie RG (2004) Chem Commun 2:188

    Article  Google Scholar 

  15. Surry DS, Buchwald SL (2010) Chem Sci 1:13

    Article  CAS  Google Scholar 

  16. Cristau HJ, Cellier PP, Spindler JF, Taillefer M (2004) Chem Eur J 10:5607

    Article  CAS  Google Scholar 

  17. Surry DS, Buchwald SL (2011) Chem Sci 2:27

    Article  CAS  Google Scholar 

  18. Maiti D, Fors BP, Henerson JL, Nakamura Y, Buchwald SL (2011) Chem Sci 2:57

    Article  CAS  Google Scholar 

  19. Islam SM, Mondal P, Tuhina K, Roy AS, Mondal S, Hossain D (2010) J Organomet Chem 695:2284–2295

    Article  CAS  Google Scholar 

  20. Islam SM, Mondal S, Roy AS, Mondal P, Mobarak M, Hossain D, Pandit P (2010) Transit Met Chem 35:305–313

    Article  CAS  Google Scholar 

  21. Islam SM, Mondal P, Roy AS, Tuhina K (2010) Transit Met Chem 35:491–499

    Article  CAS  Google Scholar 

  22. Kantam ML, Venkanna GT, Sridhar C, Sreedhar B, Choudary BM (2006) J Org Chem 71:9522

    Article  CAS  Google Scholar 

  23. Sharma BD, Bailar JC (1955) J Am Chem Soc 77:5476

    Article  Google Scholar 

  24. Sharma BD, Ray KR, Sievers RE, Bailar JC (1964) J Am Chem Soc 86:14

    Article  Google Scholar 

  25. Zhong C, Guo R, Wu Q, Zhang H (2007) React Funct Polym 67:408

    Article  CAS  Google Scholar 

  26. Zhou Y, Zhong C, He Y, Xiao L, Liu Y, Zhang H (2009) J. Inorg Organomet Polym 19:328

    Article  CAS  Google Scholar 

  27. Gupta KC, Sutar AK (2008) J Mol Catal 280:173

    Article  CAS  Google Scholar 

  28. Krishnankutty K, Ummathur MB, Sayudevi PJ (2009) Indian Chem Soc 86:325

    CAS  Google Scholar 

  29. Nakamoto N (1997) Infrared spectra and Raman spectra of inorganic and coordination compounds. Wiley, New York

    Google Scholar 

  30. Gup R, Kırkan B (2005) Spectrochim Acta A 62:1188

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  32. Maurya MR, Kumar M, Kumar A, Pessoa JC (2008) Dalton Trans 4220

  33. Karimi B, Enders D (2006) Org Lett 8:1237

    Article  CAS  Google Scholar 

  34. King RB, Sweet EM (1979) J Org Chem 44:385

    Article  CAS  Google Scholar 

  35. Johnson D, Mayer H, Minard J, Banaticla J, Miller C (1988) Inorg Chim Acta 144:167

    Article  CAS  Google Scholar 

  36. Ashton PR, Koniger R, Stoddart JF, Alker D, Harding VD (1996) J Org Chem 61:903

    Google Scholar 

  37. Choudary BM, Sridhar C, Kantam ML, Venkanna GT, Sreedhar B (2005) J Am Chem Soc 127:9948

    Article  CAS  Google Scholar 

  38. Huang YZ, Miao H, Zhang QH, Chen C, Xu J (2008) Catal Lett 122:344

    Article  CAS  Google Scholar 

  39. Rout L, Jammi S, Punniyamurthy T (2007) Org Lett 9:3397

    Article  CAS  Google Scholar 

  40. Kantam ML, Roy M, Roy S, Sreedhar B, Lal De R (2008) Catal Commun 9:2226

    Article  CAS  Google Scholar 

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Acknowledgments

We thank the Department of chemistry, University of Calcutta, for providing us the instrumental support. We gratefully acknowledge DST, New Delhi, for award of grant under its FIST program to the Department of Chemistry, University of Kalyani. SMI acknowledges the following agencies for funding: DST, CSIR, and UGC, New Delhi, India.

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Correspondence to Manirul Islam.

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Islam, M., Mondal, S., Mondal, P. et al. An efficient polymer-supported copper(II) catalyst for the N-arylation reaction of N(H)-heterocycles with aryl halides as well as arylboronic acids. Transition Met Chem 36, 447–458 (2011). https://doi.org/10.1007/s11243-011-9489-8

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