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Maghemite Supported Copper Oxide Nanocatalyst for the N–H Insertion Reaction with Ethyl Diazoacetate

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Abstract

A maghemite supported copper oxide nanocatalyst was synthesized by the wet method. XRD, ICP, SEM, VSM were used for its characterization. This system was applied as a catalyst for the N–H insertion reaction with ethyl diazoacetate. Recyclability of the catalyst was checked and its capability was studied further by using different amines. The resulted products were characterized by NMR and MS techniques.

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References

  1. Ye T, McKervey MA (1994) Chem Rev 94:1091

    Article  CAS  Google Scholar 

  2. Doyle MP, McKervey MA, Ye T (1998) Modern methods for organic synthesis with diazo compounds. Wiley, New York

    Google Scholar 

  3. Doyle MP (1986) Chem Rev 86:919

    Article  CAS  Google Scholar 

  4. Zhang Z, Wang J (2008) Tetrahedron 64:6577

    Article  CAS  Google Scholar 

  5. Clark JD, Shah AS, Peterson JC (2002) Thermochim Acta 392–393:177

    Article  Google Scholar 

  6. Cui X, Xu X, Wojtas L, Kim MM, Zhang XP (2012) J Am Chem Soc 134:19981

    Article  CAS  Google Scholar 

  7. Xia L, Lee YR (2013) Adv Synth Catal 355:2361

    Article  CAS  Google Scholar 

  8. Moody CJ, Doyle KJ (1997) Prog Heterocycl Chem 9:1

    Article  CAS  Google Scholar 

  9. Kirmse W (2002) Eur J Org Chem 2193

  10. Mejía-Oneto JM, Padwa A (2006) Org Lett 8:3275

    Article  Google Scholar 

  11. Hu W, Timmons DJ, Doyle MP (2002) Org Lett 4:901

    Article  CAS  Google Scholar 

  12. Williams MA, Hsiao CN, Miller MJ (1991) J Org Chem 56:2688

    Article  CAS  Google Scholar 

  13. Kim G, Chu-Moyer MY, Danishefsky SJ (1990) J Am Chem Soc 112:2003

    Article  CAS  Google Scholar 

  14. Gillingham D, Fei N (2013) Chem Soc Rev 42:4918

    Article  CAS  Google Scholar 

  15. Bartrum HE, Blakemore DC, Moody CJ, Hayes CJ (2011) Chem Eur J 17:9586

    Article  CAS  Google Scholar 

  16. Davis FA, Yang B, Deng J (2003) J Org Chem 68:5147

    Article  CAS  Google Scholar 

  17. Moody CJ, Ferris L, Haigh D, Swann E (1997) Chem Commun 2391

  18. Buck RT, Clarke PA, Coe DM, Drysdale MJ, Ferris L, Haigh D, Moody CJ, Pearson ND, Swann E (2000) Chem Eur J 6:2160

    Article  CAS  Google Scholar 

  19. Salzmann TN, Ratcliffe RW, Christensen BG, Bouffard FA (1980) J Am Chem Soc 102:6161

    Article  CAS  Google Scholar 

  20. Lee SH, Clapham B, Koch G, Zimmermann J, Janda KD (2003) J Comb Chem 5:188

    Article  CAS  Google Scholar 

  21. Shi B, Blake AJ, Lewis W, Campbell IB, Judkins BD, Moody CJ (2010) J Org Chem 75:152

    Article  CAS  Google Scholar 

  22. Yang M, Wang X, Li H, Livant P (2001) J Org Chem 66:6729

    Article  CAS  Google Scholar 

  23. Bachmann S, Fielenbach D, Jørgensen KA (2004) Org Biomol Chem 2:3044

    Article  CAS  Google Scholar 

  24. Liu B, Zhu SF, Chao Chen WZ, Zhou QL (2007) J Am Chem Soc 129:5834

    Article  CAS  Google Scholar 

  25. Xu B, Zhu SF, Xie XL, Shen JJ, Zhou QL (2011) Angew Chem Int Ed 50:11483

    Article  CAS  Google Scholar 

  26. Hou Z, Wang J, He P, Wang J, Qin B, Liu X, Lin L, Feng X (2010) Angew Chem Int Ed 49:4763

    Article  CAS  Google Scholar 

  27. Morilla ME, Díaz-Requejo MM, Belderrain TR, Nicasio MC, Trofimenko S, Pérez PJ (2002) Chem Commun 2998

  28. Kantam ML, Neelima B, Reddy CV (2006) J Mol Catal A 256:269

    Article  CAS  Google Scholar 

  29. Baumann LK, Mbuvi HM, Du G, Woo LK (2007) Organometallics 26:3995

    Article  CAS  Google Scholar 

  30. Le Maux P, Nicolas I, Chevance S, Simonneaux G (2010) Tetrahedron 66:4462

    Article  Google Scholar 

  31. Zhu Z, Espenson JH (1996) J Am Chem Soc 118:9901

    Article  CAS  Google Scholar 

  32. Varala R, Enugala R, Adapa SR (2008) Monatsh Chem 139:1369

    Article  CAS  Google Scholar 

  33. Kantam ML, Laha S, Yadav J, Jha S (2009) Tetrahedron Lett 50:4467

    Article  CAS  Google Scholar 

  34. Moore JA, Medeiros RW (1959) J Am Chem Soc 81:6026

    Article  CAS  Google Scholar 

  35. Akbari J, Ebrahimi A, Heydari A (2014) Tetrahedron Lett 55:5417

    Article  CAS  Google Scholar 

  36. Ferrand Y, Le Maux P, Simonneaux G (2005) Tetrahedron Asymmetry 16:3829

    Article  CAS  Google Scholar 

  37. Rechavi D, Lemaire M (2002) Chem Rev 102:3467

    Article  CAS  Google Scholar 

  38. Fraile JM, García JI, Mayoral JA (2008) Coord Chem Rev 252:624–646

    Article  CAS  Google Scholar 

  39. Candeias NRCA, Gois PM (2012) Org Biomol Chem 10:3357

    Article  CAS  Google Scholar 

  40. Takeda K, Oohara T, Shimada N, Nambu H, Hashimoto S (2011) Chem Eur J 17:13992

    Article  CAS  Google Scholar 

  41. Abu Elfotoh AM, Phomkeona K, Shibatomi K, Iwasa S (2010) Angew Chem Int Ed 49:8439

    Article  CAS  Google Scholar 

  42. Lim J, Riduan SN, Lee SS, Ying JY (2008) Adv Synth Catal 350:1295

    Article  CAS  Google Scholar 

  43. Cano R, Ramón DJ, Yus M (2011) J Org Chem 76:5547

    Article  CAS  Google Scholar 

  44. Fraile JM, Le Jeune K, Mayoral JA, Ravasio N, Zaccheria F (2013) Org Biomol Chem 11:4327

    Article  CAS  Google Scholar 

  45. Fraile JM, Mayoral JA, Muñoz A, Santafé-Valero J (2013) Tetrahedron 69:7360

    Article  CAS  Google Scholar 

  46. Fraile JM, Mayoral JA, Ravasio N, Roldán M, Sordelli L, Zaccheria F (2011) J Catal 281:273

    Article  CAS  Google Scholar 

  47. Liu X, Liu Y, Li X, Xiang S, Zhang Y, Ying P, Wei Z, Li C (2003) Appl Catal A 239:279

    Article  CAS  Google Scholar 

  48. Cano R, Yus M, Ramón DJ (2012) Tetrahedron 68:1393

    Article  CAS  Google Scholar 

  49. Ma’mani L, Heydari A, Sheykhan M (2010) Appl Catal A 384:122

    Article  Google Scholar 

  50. Cudennec Y, Lecerf A (2003) Solid State Sci 5:1471

    Article  CAS  Google Scholar 

  51. Aller E, Buck RT, Drysdale MJ, Ferris L, Haigh D, Moody CJ, Pearson ND, Sanghera JB (1996) J Chem Soc Perkin Trans 1:2879

    Article  Google Scholar 

  52. Galardon E, Le Maux P, Simonneaux G (1997) J Chem Soc Perkins Trans 1:2455

    Article  Google Scholar 

  53. Aviv I, Gross Z (2008) Chem Eur J 14:3995

    Article  CAS  Google Scholar 

  54. Hansen SR, Spangler JE, Hansen JH, Davies HML (2012) Org Lett 14:4626

    Article  CAS  Google Scholar 

  55. Singh SB, Mehrotra KN (1981) Can J Chem 59:2475

    Article  CAS  Google Scholar 

  56. Fructos MR, Belderrain TR, Nicasio MC, Nolan SP, Kaur H, Díaz-Requejo MM, Pérez PJ (2004) J Am Chem Soc 126:10846

    Article  CAS  Google Scholar 

  57. Li GY, Che CM (2004) Org Lett 6:1621

    Article  CAS  Google Scholar 

  58. Rivilla I, Sameera WMC, Alvarez E, Díaz-Requejo MM, Maseras F, Pérez PJ (2013) Dalton Trans 42:4132

    Article  CAS  Google Scholar 

  59. Forbes AD, Wood J (1971) J Chem Soc B 646

  60. Pomerantz M, Rooney P (1989) Energy Fuels 3:357

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank Tarbiat Modares University and Iran Nanotechnology Initiative Council for financial support of this research.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Ali Ebrahimi & Akbar Heydari

  2. Department of Environmental Health Engineering, Iran University of Medical Sciences, Tehran, Iran

    Ali Esrafili

Authors
  1. Ali Ebrahimi
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  2. Akbar Heydari
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  3. Ali Esrafili
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Corresponding author

Correspondence to Akbar Heydari.

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Ebrahimi, A., Heydari, A. & Esrafili, A. Maghemite Supported Copper Oxide Nanocatalyst for the N–H Insertion Reaction with Ethyl Diazoacetate. Catal Lett 144, 2204–2209 (2014). https://doi.org/10.1007/s10562-014-1391-5

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  • DOI: https://doi.org/10.1007/s10562-014-1391-5

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