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Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and magnetically recoverable catalyst for N-arylation of imidazole with aryl halides

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Abstract

The Fe3O4@SiO2/Salen-Cu(II) nanocatalyst is reported as a thermally and air-stable, economical, and magnetically recoverable heterogeneous catalyst for the selective and efficient N-(hetero)arylation of imidazole. Only by adding a small amount of the catalyst (0.4 mol% Cu) to the reactants and heating under air, the new presented method provides a variety of functionalized and hindered N-(hetero)arylimidazoles in good to excellent yields within short reaction times. The catalyst could be easily recovered with the aid of a permanent magnet and reused up to five consecutive runs without significant loss of activity. Also, the leaching of Cu was negligible after the fifth recycle. Particularly, using either (hetero)aryl iodides or bromides as arylating agents and the need of only small amount of the magnetically recoverable heterogeneous copper-based nanocatalyst make this method low-cost, environmentally benign, and easy to use.

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References

  1. Grauer A, Späth A, Ma D, König B (2009) Chem Asian J 4:1134

    Article  CAS  PubMed  Google Scholar 

  2. Güngör T, Fouquet A, Teulon JM, Provost D, Cazes M, Cloarec A (1992) J Med Chem 35:4455

    Article  PubMed  Google Scholar 

  3. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    Article  CAS  Google Scholar 

  4. Sircar I, Duell BL, Bobowski G, Bristol JA, Evans DB (1985) J Med Chem 28:1405

    Article  CAS  PubMed  Google Scholar 

  5. Lo YS, Nolan JC, Maren TH, Welstead WJ Jr, Gripshover DF, Shamblee DA (1992) J Med Chem 35:4790

    Article  CAS  PubMed  Google Scholar 

  6. Rani N, Sharma A, Singh R (2013) Mini Rev Med Chem 13:1812

    Article  CAS  PubMed  Google Scholar 

  7. Heeres J, Backx LJJ, Mostmans JH, Cutsem JV (1979) J Med Chem 22:1003

    Article  CAS  PubMed  Google Scholar 

  8. Al-Masoudi NA, Al-Soud YA, Kalogerakis A, Pannecouque C, De Clercq E (2006) Chem Biodivers 3:515

    Article  CAS  PubMed  Google Scholar 

  9. Leeson PD, Springthorpe B (2007) Nat Rev Drug Discov 6:881

    Article  CAS  PubMed  Google Scholar 

  10. Nyce GW, Glauser T, Connor EF, Möck A, Waymouth RM, Hedrick JL (2003) J Am Chem Soc 125:3046

    Article  CAS  PubMed  Google Scholar 

  11. Harkal S, Rataboul F, Zapf A, Fuhrmann C, Riermeier T, Monsees A, Beller M (2004) Adv Synth Catal 346:1742

    Article  CAS  Google Scholar 

  12. Suárez-Pantiga S, Rubio E, Alvarez-Rúa C, González JM (2009) Org Lett 11:13

    Article  CAS  PubMed  Google Scholar 

  13. Venuti MC, Stephenson RA, Alvarez R, Bruno JJ, Strosberg AM (1988) J Med Chem 31:2136

    Article  CAS  PubMed  Google Scholar 

  14. Priyarega S, Raja DS, Babu SG, Karvembu R, Hashimoto T, Endo A, Natarajan K (2012) Polyhedron 34:143

    Article  CAS  Google Scholar 

  15. Kiyomori A, Marcoux JF, Buchwald SL (1999) Tetrahedron Lett 40:2657

    Article  CAS  Google Scholar 

  16. Wu CD, Li L, Shi LX (2009) Dalton Trans 2009:6790

    Article  CAS  Google Scholar 

  17. López-Alvarado P, Avendaño C, Menéndez JC (1995) J Org Chem 60:5678

    Article  Google Scholar 

  18. Kang SK, Lee SH, Lee D (2000) Synlett 2000:1022

    Article  Google Scholar 

  19. Fedorov AY, Finet JP (1999) Tetrahedron Lett 40:2747

    Article  CAS  Google Scholar 

  20. Farahat AA, Boykin DW (2014) Tetrahedron Lett 55:3049

    Article  CAS  Google Scholar 

  21. Kantam ML, Yadav J, Laha S, Sreedhar B, Jha S (2007) Adv Synth Catal 349:1938

    Article  CAS  Google Scholar 

  22. Yang Q, Wang Y, Yang L, Zhang M (2013) Tetrahedron 69:6230

    Article  CAS  Google Scholar 

  23. Xu ZL, Li HX, Ren ZG, Du WY, Xu WC, Lang JP (2011) Tetrahedron 67:5282

    Article  CAS  Google Scholar 

  24. Liu YS, Liu Y, Ma XW, Liu P, Xie JW, Dai B (2014) Chin Chem Lett 25:775

    Article  CAS  Google Scholar 

  25. Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset JM (2011) Chem Rev 111:3036

    Article  CAS  PubMed  Google Scholar 

  26. Astruc D, Lu F, Aranzaes JR (2005) Angew Chem Int Ed 44:7852

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  28. Safaei-Ghomi J, Zahedi S, Ghasemzadeh MA (2014) Monatsh Chem 145:1191

    Article  CAS  Google Scholar 

  29. Mohaqeq M, Safaei-Ghomi J (2015) Monatsh Chem 146:1581

    Article  CAS  Google Scholar 

  30. Alonso F, Riente P, Sirvent JA, Yus M (2010) Appl Catal A Gen 378:42

    Article  CAS  Google Scholar 

  31. Rostamizadeh S, Abdollahi F, Shadjou N, Amani AM (2013) Monatsh Chem 144:1191

    Article  CAS  Google Scholar 

  32. Gupta AK, Gupta M (2005) Biomaterials 26:3995

    Article  CAS  PubMed  Google Scholar 

  33. Harrison RJ, Dunin-Borkowski RE, Putnis A (2002) Proc Natl Acad Sci USA 99:16556

    Article  CAS  PubMed  Google Scholar 

  34. Wu W, He Q, Jiang C (2008) Nanoscale Res Lett 3:397

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Esmaeilpour M, Sardarian AR (2014) Green Chem Lett Rev 7:301

    Article  CAS  Google Scholar 

  36. Esmaeilpour M, Javidi J, Nowroozi-Dodeji F, Hassannezhad H (2014) J Iran Chem Soc 11:1703

    Article  CAS  Google Scholar 

  37. Esmaeilpour M, Javidi J (2015) J Chin Chem Soc 62:614

    Article  CAS  Google Scholar 

  38. Esmaeilpour M, Javidi J (2015) J Chin Chem Soc 62:328

    Article  CAS  Google Scholar 

  39. Esmaeilpour M, Javidi J, Zahmatkesh S (2016) Appl Organomet Chem 30:897

    Article  CAS  Google Scholar 

  40. Panda N, Jena AK, Mohapatra S, Rout SR (2011) Tetrahedron Lett 52:1924

    Article  CAS  Google Scholar 

  41. Nador F, Volpe MA, Alonso F, Radivoy G (2014) Tetrahedron 70:6082

    Article  CAS  Google Scholar 

  42. Sivakami R, Babu SG, Dhanuskodi S, Karvembu R (2015) RSC Adv 5:8571

    Article  CAS  Google Scholar 

  43. Liu Y, Zhang Q, Ma X, Liu P, Xie J, Dai B, Liu Z (2013) Int J Org Chem 3:185

    Article  CAS  Google Scholar 

  44. Dehghani F, Sardarian AR, Esmaeilpour M (2013) J Organomet Chem 743:87

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  46. Emel’yanenko VN, Kaliner M, Strassner T, Verevkin SP (2017) Fluid Phase Equilib 433:40

    Article  CAS  Google Scholar 

  47. Lv X, Wang Z, Bao W (2006) Tetrahedron 62:4756

    Article  CAS  Google Scholar 

  48. Altman RA, Buchwald SL (2006) Org Lett 8:2779

    Article  CAS  PubMed  Google Scholar 

  49. Yang K, Qiu Y, Li Z, Wang Z, Jiang S (2011) J Org Chem 76:3151

    Article  CAS  PubMed  Google Scholar 

  50. Inamoto K, Nozawa K, Kadokawa J, Kondo Y (2012) Tetrahedron 68:7794

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  52. Xue F, Cai C, Sun H, Shen Q, Rui J (2008) Tetrahedron Lett 49:4386

    Article  CAS  Google Scholar 

  53. Joseph PJA, Priyadarshini S, Kantam ML, Maheswaran H (2011) Catal Sci Technol 1:234

    Article  CAS  Google Scholar 

  54. Hosseini-Sarvari M, Moeini F (2014) RSC Adv 4:7321

    Article  CAS  Google Scholar 

  55. Esmaeilpour M, Sardarian AR, Jarrahpour A, Ebrahimi E, Javidi J (2016) RSC Adv 6:43376

    Article  CAS  Google Scholar 

  56. Deng Y, Qi D, Deng C, Zhang X, Zhao D (2008) J Am Chem Soc 130:28

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We would like to gratefully acknowledge financial support of this work by research council of Shiraz University.

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Authors and Affiliations

  1. Chemistry Department, College of Sciences, Shiraz University, Shiraz, 71946 84795, Iran

    Ali Reza Sardarian, Neda Zohourian-Mashmoul & Mohsen Esmaeilpour

Authors
  1. Ali Reza Sardarian
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  2. Neda Zohourian-Mashmoul
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  3. Mohsen Esmaeilpour
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Correspondence to Ali Reza Sardarian.

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Sardarian, A.R., Zohourian-Mashmoul, N. & Esmaeilpour, M. Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and magnetically recoverable catalyst for N-arylation of imidazole with aryl halides. Monatsh Chem 149, 1101–1109 (2018). https://doi.org/10.1007/s00706-018-2148-4

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  • DOI: https://doi.org/10.1007/s00706-018-2148-4

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