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Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole

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Abstract

A study of copper-mediated C–heteroatom especially C–N and C–O bond formations using simpler methodologies has been carried out. In the present work, acetylation of various substrates such as amines, phenols and alcohols; synthesis of 2,4,5-trisubstituted imidazole is done using simple and easily available starting materials. Copper (I) oxide was synthesized in situ by the reduction of Fehling’s solution with glucose followed by its anchoring onto different supports like silica, HAP, basic alumina and cellulose. Comparison and contrasts between the reactivity of copper (I) oxide supported onto different supports for these reactions are made. The reactivity of copper (I) oxide seems to be largely dependent on the nature of support and the most active catalyst for a particular reaction was further characterized by different spectroscopic techniques such as FTIR, XRD, TGA, XPS, SEM, TEM and AAS. The catalysts were found to be stable, easily recyclable without any significant loss in activity.

Graphical abstract

Applications of solid supported copper (I) oxides (where solid support is silica, HAP, cellulose and basic alumina) are studied for various organic transformations with special emphasis on C–N and C–O bond formation reactions.

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References

  1. J.F. Hartwig, Nature 455, 314 (2008)

    Article  CAS  Google Scholar 

  2. G.A. Artamkina, M.V. Ermolina, I.P. Beletskaya, Mendeleev Commun. 13, 158 (2003)

    Article  Google Scholar 

  3. J.F. Hartwig, Synlett. 1997, 329 (1997)

    Article  Google Scholar 

  4. J.F. Hartwig, Acc. Chem. Res. 31, 852 (1998)

    Article  CAS  Google Scholar 

  5. C.G. Frost, P. Mendonca, J. Chem. Soc. Perkin Trans. 1, 2615 (1998)

    Article  Google Scholar 

  6. A.J. Belfield, G.R. Brown, A.J. Foubister, Tetrahedron 55, 11399 (1999)

    Article  CAS  Google Scholar 

  7. D. Prim, J.M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 58, 2041 (2002)

    Article  CAS  Google Scholar 

  8. J.P. Wolfe, S. Wagaw, J.-F. Marcoux, S.L. Buchwald, Acc. Chem. Res. 31, 805 (1998)

    Article  CAS  Google Scholar 

  9. J.F. Hartwig, Angew. Chem. Int. Ed. Engl. 37, 2046 (1998)

    Article  CAS  Google Scholar 

  10. B.H. Yang, S.L. Buchwald, J. Organomet. Chem. 576, 125 (1999)

    Article  CAS  Google Scholar 

  11. Y.R. de Miguel, E. Brule, R.G. Margue, J. Chem. Soc. Perkin Trans. 1, 3085 (2001)

    Article  Google Scholar 

  12. B.A. Lorsbach, M.J. Kurth, Chem. Rev. 99, 1549 (1999)

    Article  CAS  Google Scholar 

  13. C.A. Parrish, S.L. Buchwald, J. Org. Chem. 66, 3820 (2001)

    Article  CAS  Google Scholar 

  14. M. Gupta, S. Paul, R. Gupta, Chin. J. Catal. 35, 444 (2014)

    Article  CAS  Google Scholar 

  15. H.M. Wei, H.B. Gong, L. Chen, M. Zi, B.Q. Cao, J. Phys. Chem. C 116, 10510 (2012)

    Article  CAS  Google Scholar 

  16. I. Baker, R.S. Gibbs, Ind. Eng. Chem. Anal. Ed. 15, 505 (1943)

    Article  CAS  Google Scholar 

  17. W. Sun, W. Sun, Y. Zhao, Y. Chu, J. Solid, State. Chem. 184, 1638 (2011)

    Article  CAS  Google Scholar 

  18. C.H. Kuo, M.H. Huang, Nano. Today 5, 106 (2010)

    Article  CAS  Google Scholar 

  19. Y.X. Wang, X.F. Tang, Z.G. Yang, Colloids Surf. A Physicochem. Eng. Asp. 388, 38 (2011)

    Article  CAS  Google Scholar 

  20. J.H. Lee, S.K. Hong, W.B. Ko, J. Ind. Eng. Chem. 16, 564 (2010)

    Article  CAS  Google Scholar 

  21. H.L. Ruiz, J.E.C. de la Pedro, S.R. Lima, I.P. Perez, B.V.R. Sanchez, R. Santillan, O. Cereno, ARKIVOC iii, 139 (2013)

    Google Scholar 

  22. V. Beneteau, A. Olmos, T. Boningari, J. Sommer, P. Pale, Tetrahedron Lett. 51, 3673 (2010)

    Article  CAS  Google Scholar 

  23. X.Y. Yan, X.L. Tong, Y.F. Zhang, X.D. Han, Y.Y. Wang, G.Q. Jin, Y. Qin, X.Y. Guo, Chem. Commun. 48, 1892 (2012)

    Article  CAS  Google Scholar 

  24. K.V.R. Chary, G.V. Sagar, D. Naresh, K.K. Seela, B. Sridhar, J. Phys. Chem. B. 109, 9437 (2005)

    Article  CAS  Google Scholar 

  25. A.R. Hajipour, F. Mohammadsaleh, J. Iran. Chem. Soc. (2015). doi:10.1007/s13738-015-0599-7

    Google Scholar 

  26. S.H. Tohidi, Int. J. Nanosci. Nanotechnol. 7, 7 (2011)

    Google Scholar 

  27. Y. Qian, F. Ye, J. Xu, Z.G. Le, Int. J. Electrochem. Sci. 7, 10063 (2012)

    CAS  Google Scholar 

  28. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd edn. (Wiley, New York, 1999)

    Book  Google Scholar 

  29. P.J. Kocieński, Protecting Groups (Georg Thieme Verlag, New York, 1994)

    Google Scholar 

  30. S. Naik, G. Bhattacharjya, V.R. Kavala, B.K. Patel, ARKIVOC i, 55 (2004)

    Google Scholar 

  31. P. Phukan, Tetrahedron Lett. 45, 4785 (2004)

    Article  CAS  Google Scholar 

  32. R.H. Baker, F.G. Bordwell, Organic Synthesis Collective, vol. III (Wiley, New York, 1995), p. 141

    Google Scholar 

  33. S.V. Pansare, M.G. Malusare, A.N. Rai, Synth. Commun. 30, 2587 (2000)

    Article  CAS  Google Scholar 

  34. I.M. Baltork, H. Aliyan, A.R. Khosropour, Tetrahedron 57, 5851 (2001)

    Article  Google Scholar 

  35. S.K. De, Tetrahedron Lett. 45, 2919 (2004)

    Article  Google Scholar 

  36. A.K. Chakraborti, R. Gulhane, Tetrahedron Lett. 44, 6749 (2003)

    Article  CAS  Google Scholar 

  37. R. Dalpozzo, A.D. Nino, L. Maiuolo, A. Procopiou, M. Nardi, G. Bartoli, R. Romeo, Tetrahedron Lett. 44, 5621 (2003)

    Article  CAS  Google Scholar 

  38. M.L. Kantam, K. Aziz, P.R. Likhar, Catal. Commun. 7, 484 (2006)

    Article  CAS  Google Scholar 

  39. R. Ghosh, S. Maiti, A.K. Chakraborty, Tetrahedron Lett. 46, 147 (2005)

    Article  CAS  Google Scholar 

  40. A. Kamal, M. Naseer, A. Khan, K.S. Reddy, Y.V.V. Srikanth, T. Krishnaji, Tetrahedron Lett. 48, 3813 (2007)

    Article  CAS  Google Scholar 

  41. B. Das, P. Thirupathi, J. Mol. Catal. A: Chem. 269, 12 (2007)

    Article  CAS  Google Scholar 

  42. T.S. Reddy, M. Narasimhulu, N. Suryakiran, K.C. Mahesh, K. Ashalatha, Y. Venkateswarlu, Tetrahedron Lett. 47, 6825 (2006)

    Article  CAS  Google Scholar 

  43. J.S. Yadav, A.V. Narsaiah, A.K. Basak, P.R. Goud, D. Sreenu, K. Nagaiah, J. Mol. Catal. A: Chem. 255, 78 (2006)

    Article  CAS  Google Scholar 

  44. J.K. Joseph, S.L. Jain, B. Sain, J. Mol. Catal. A: Chem. 267, 108 (2007)

    Article  CAS  Google Scholar 

  45. K. Shyamprasad, S.Z.M. Shamshuddin, V.T. Vasantha, J. Porous Mater. 21, 1079 (2014)

    Article  CAS  Google Scholar 

  46. S. Farhadi, K. Jahanara, A. Sepahdar, J. Iran. Chem. Soc. 11, 1103 (2014)

    Article  CAS  Google Scholar 

  47. F. Dehghani, A.R. Sardarian, M.M. Doroodmand, J. Iran. Chem. Soc. 11, 673 (2014)

    Article  CAS  Google Scholar 

  48. S. Farhadi, K. Jahanara, Chin. J. Catal. 35, 368 (2014)

    Article  CAS  Google Scholar 

  49. T.E. Kristensen, Beilstein J. Org. Chem. 11, 446 (2015)

    Article  CAS  Google Scholar 

  50. R.K. Sodhi, V. Kumar, S. Paul, Open Catalysis J. 6, 1 (2013)

    Article  CAS  Google Scholar 

  51. A.A. Marzouk, V.M. Abbasov, A.H. Talybov, Chem. J. 2, 179 (2012)

    CAS  Google Scholar 

  52. S.V. Nalage, M.B. Kalyankar, V.S. Patil, S.V. Bhosale, S.U. Deshmukh, R.P. Pawar, Open Catalysis J. 3, 58 (2010)

    Article  CAS  Google Scholar 

  53. M. Gupta, M. Gupta, S. Paul, V.K. Gupta, R. Khajuria, Monatsh. Chem. 146, 143 (2015)

    Article  CAS  Google Scholar 

  54. G.J. Poinem, R. Brundavanam, X.T. Le, S. Diordjevic, M. Prokic, D. Fawcett, Int. J. Nanomed. 6, 2083 (2011)

    Google Scholar 

  55. A. Chandrasekar, S. Sagadevan, A. Dakshnamoorthy, Int. J. Phys. Sci. 8, 1639 (2013)

    Google Scholar 

  56. A. Singh, K.M. Purohit, J. Biotechnol. Biomater. 2, 104 (2011)

    Article  Google Scholar 

  57. S. Paul, P. Nanda, R. Gupta, A. Loupy, Tetrahedron Lett. 43, 4261 (2002)

    Article  CAS  Google Scholar 

  58. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, 5th edn. (Longman-ELBS, London, 1991), p. 1370

    Google Scholar 

  59. Handbook of Fine Chemicals, Sigma Aldrich (Advancing Science), vol. 2007–2008, p. 629

  60. G. Brahmachari, S. Laskar, S. Sarkar, Indian J. Chem. 49B, 1274 (2010)

    CAS  Google Scholar 

  61. Research Chemicals, Metals and Materials, Alfa aesar (A Johnson Matthey Company), vol. 2011–2013, p. 1124

  62. R. Gupta, V. Kumar, M. Gupta, S. Paul, R. Gupta, Indian J. Chem. 47B, 1739 (2008)

    CAS  Google Scholar 

  63. L.R. Steffel, T.J. Cashman, M.H. Reutershanand, B.R. Linton, J. Am. Chem. Soc. 129, 12956 (2007)

    Article  CAS  Google Scholar 

  64. S. Farhadi, S. Panahandehjoo, Eur. J. Chem. 1, 335 (2010)

    Article  CAS  Google Scholar 

  65. T.S. Jin, Y.R. Ma, T.S. Li, Z.H. Zhang, G.B. Duan, Indian J. Chem. 38B, 109 (1999)

    CAS  Google Scholar 

  66. M.M. Mojtahedi, M.S. Abaee, M. Javadpour, Phosphorus Sulfur Silicon Relat. Elem. 185, 2362 (2010)

    Article  CAS  Google Scholar 

  67. J. Safari, S.D. Khalili, S.H. Banitaba, J. Chem. Sci. 122, 437 (2010)

    Article  CAS  Google Scholar 

  68. M.M. Heravi, M. Zakeri, H. Haghi, Synth. React. Inorg. Metal-Org. Nano-Metal Chem. 41, 1310 (2011)

    Article  CAS  Google Scholar 

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Acknowledgments

We are grateful to Director, SAIF, Punjab University, Chandigarh, for TEM and XRD and also to Head, SAIF, IIT Bombay, for recording SEM images. We extend our sincere thanks to UGC, New Delhi, for financial support to purchase FTIR; awarding Major Research Project F 41‐281/2012 (SR), and Prof. R.K. Bamezai, Department of Chemistry, University of Jammu, for recording TGA.

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  1. Department of Chemistry, University of Jammu, Jammu, 180 006, India

    Manjulla Gupta & Monika Gupta

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  1. Manjulla Gupta
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Correspondence to Monika Gupta.

Electronic supplementary material

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Supplementary material 1 (DOC 1405 kb) Supplementary information 1: Spectral details of all the compounds

13738_2015_730_MOESM2_ESM.doc

Supplementary material 2 (DOC 3046 kb) Supplementary information 1: 1H NMR and 13C NMR of some selected N-acetylated, O-acetylated products and 2,4,5-trisubstituted imidazoles

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Gupta, M., Gupta, M. Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole. J IRAN CHEM SOC 13, 231–241 (2016). https://doi.org/10.1007/s13738-015-0730-9

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