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Sulfated polyborate-catalyzed N-formylation of amines: a rapid, green and efficient protocol

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Abstract

A rapid, green and efficient method for N-formylation reaction of various amines with formic acid in the presence of sulfated polyborate catalyst under solvent-free conditions has been described. The catalyst has the advantage of mild Bronsted as well as Lewis acid character. The catalyst is recyclable with no significant loss in catalytic activity. The present protocol is advantageous due to its solvent-free condition, short reaction time, high yields, easy workup and ability to tolerate a variety of functional groups.

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References

  1. A.C. Shekhar, A.R. Kumar, G. Sathaiah, V.L. Paul, M. Sridhar, P.S. Rao, Tetrahedron Lett. 50, 7099 (2009)

    Article  CAS  Google Scholar 

  2. A. Jackson, O. Meth-Cohn, J. Chem. Soc. Chem. Commun. 13, 1319 (1995)

    Article  Google Scholar 

  3. K. Kawashima, M. Sisido, K. Ichimura, Chem. Lett. 24, 491 (1995)

    Article  Google Scholar 

  4. B.C. Chen, M.S. Bednarz, R. Zhao, J.E. Sundeen, P. Chen, Z. Shen, A.P. Skoumbourdis, J.C. Barrish, Tetrahedron Lett. 41, 5453 (2000)

    Article  CAS  Google Scholar 

  5. S. Kobayashi, M. Yasuda, I. Hachiya, Chem. Lett. 25, 407 (1996)

    Article  Google Scholar 

  6. S. Kobayashi, K. Nishio, J. Org. Chem. 59, 6620 (1994)

    Article  CAS  Google Scholar 

  7. I.M. Downie, M.J. Earle, H. Heaney, K.F. Shuhaibar, Tetrahedron 49, 4015 (1993)

    Article  CAS  Google Scholar 

  8. M. Viji, R. Nagarajan, J. Chem. Sci. 126, 1075 (2014)

    Article  CAS  Google Scholar 

  9. J. Martinez, J. Laur, Synthesis (Stuttg) 1982, 979 (1982)

    Article  Google Scholar 

  10. G.P. Anderson, Life Sci. 52, 2145 (1993)

    Article  CAS  Google Scholar 

  11. K. Tanaka, Rheumatol. Rep. 1, 11 (2009)

    Article  CAS  Google Scholar 

  12. M.-L. Volvert, S. Seyen, M. Piette, B. Evrard, M. Gangolf, J.-C. Plumier, L. Bettendorff, BMC Pharmacol. 8, 10 (2008)

    Article  Google Scholar 

  13. F.F. Blicke, C.-J. Lu, J. Am. Chem. Soc. 74, 3933 (1952)

    Article  Google Scholar 

  14. M. Waki, J. Meienhofer, J. Org. Chem. 42, 2019 (1977)

    Article  CAS  Google Scholar 

  15. F.M.F. Chen, N.L. Benoiton, Synthesis (Stuttg) 1979, 709 (1979)

    Article  Google Scholar 

  16. L. De Luca, G. Giacomelli, A. Porcheddu, M. Salaris, Synlett 2004, 2570 (2004)

    Article  Google Scholar 

  17. W. Duczek, J. Deutsch, S. Vieth, H.-J. Niclas, Synthesis (Stuttg) 1996, 37 (1996)

    Article  Google Scholar 

  18. P. Strazzolini, A.G. Giumanini, S. Cauci, Tetrahedron 46, 1081 (1990)

    Article  CAS  Google Scholar 

  19. P.G. Reddy, G.D.K. Kumar, S. Baskaran, Tetrahedron Lett. 41, 9149 (2000)

    Article  Google Scholar 

  20. G. Brahmachari, S. Laskar, Tetrahedron Lett. 51, 2319 (2010)

    Article  CAS  Google Scholar 

  21. B. Das, M. Krishnaiah, P. Balasubramanyam, B. Veeranjaneyulu, D.N. Kumar, Tetrahedron Lett. 49, 2225 (2008)

    Article  CAS  Google Scholar 

  22. L. Zhang, Z. Han, X. Zhao, Z. Wang, K. Ding, Angew. Chem. Int. Ed. Engl. 54, 6186 (2015)

    Article  CAS  Google Scholar 

  23. P. Daw, S. Chakraborty, G. Leitus, Y. Diskin-Posner, Y. Ben-David, D. Milstein, ACS Catal. 8, 2500 (2017)

    Article  Google Scholar 

  24. M. Mihara, Y. Ishino, S. Minakata, M. Komatsu, Synthesis (Stuttg) 2003, 2317 (2003)

    Google Scholar 

  25. M. Bhojegowd, M. Reddy, A. Nizam, M.A. Pasha, Chin. J. Catal. 31, 518 (2010)

    Article  CAS  Google Scholar 

  26. M.H. Sarvari, H. Sharghi, J. Org. Chem. 71, 6652 (2006)

    Article  Google Scholar 

  27. S.M. Sajadi, M. Maham, A. Rezaei, Lett. Org. Chem. 11, 49 (2014)

    Article  CAS  Google Scholar 

  28. M.B.M. Reddy, S. Ashoka, G.T. Chandrappa, M.A. Pasha, Catal. Lett. 138, 82 (2010)

    Article  CAS  Google Scholar 

  29. S. Bahari, B. Mohammadi-Aghdam, S.M. Sajadi, F. Zeidali, Bull. Korean Chem. Soc. 33, 2251 (2012)

    Article  CAS  Google Scholar 

  30. D. Habibi, M. Nasrollahzadeh, H. Sahebekhtiari, J. Mol. Catal. A: Chem. 378, 148 (2013)

    Article  CAS  Google Scholar 

  31. J.-G. Kim, D. Jang, Synlett 2010, 1231 (2010)

    Article  Google Scholar 

  32. B. Krishnakumar, M. Swaminathan, J. Mol. Catal. A Chem. 334, 98 (2011)

    Article  CAS  Google Scholar 

  33. S.P. Pathare, R.V. Sawant, K.G. Akamanchi, Tetrahedron Lett. 53, 3259 (2012)

    Article  CAS  Google Scholar 

  34. M.I. Ansari, M.K. Hussain, N. Yadav, P.K. Gupta, K. Hajela, Tetrahedron Lett. 53, 2063 (2012)

    Article  CAS  Google Scholar 

  35. L. Ma’mani, M. Sheykhan, A. Heydari, M. Faraji, Y. Yamini, Appl. Catal. A Gen. 377, 64 (2010)

    Article  Google Scholar 

  36. Z. Chen, R. Fu, W. Chai, H. Zheng, L. Sun, Q. Lu, R. Yuan, Tetrahedron 70, 2237 (2014)

    Article  CAS  Google Scholar 

  37. S.P. Satasia, P.N. Kalaria, D.K. Raval, J. Mol. Catal. A Chem. 391, 41 (2014)

    Article  CAS  Google Scholar 

  38. V.K. Das, R.R. Devi, P.K. Raul, A.J. Thakur, Green Chem. 14, 847 (2012)

    Article  CAS  Google Scholar 

  39. M. Hosseini-Sarvari, E. Safary, A. Jarrahpour, R. Heiran, Comptes Rendus Chim. 15, 980 (2012)

    Article  CAS  Google Scholar 

  40. M. Kooti, E. Nasiri, J. Mol. Catal. A Chem. 406, 168 (2015)

    Article  CAS  Google Scholar 

  41. F. Shirini, M. Mazloumi, M. Seddighi, Res. Chem. Intermed. 42, 1759 (2016)

    Article  CAS  Google Scholar 

  42. D. Habibi, P. Rahmani, Z. Akbaripanah, J. Chem. 2013, 1 (2012)

    Google Scholar 

  43. M. Seddighi, F. Shirini, M. Mamaghani, J. Iran. Chem. Soc. 12, 433 (2015)

    Article  CAS  Google Scholar 

  44. X.J. Yang, Y. Sen, Zhang. Res. Chem. Intermed. 39, 2843 (2013)

    Article  CAS  Google Scholar 

  45. C.K. Khatri, D.S. Rekunge, G.U. Chaturbhuj, New J. Chem. 40, 10412 (2016)

    Article  CAS  Google Scholar 

  46. C.K. Khatri, V.B. Satalkar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 694 (2017)

    Article  CAS  Google Scholar 

  47. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci. 129, 141 (2017)

    Article  CAS  Google Scholar 

  48. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 1240 (2017)

    Article  CAS  Google Scholar 

  49. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci. 129, 415 (2017)

    Article  CAS  Google Scholar 

  50. C.K. Khatri, A.S. Mali, G.U. Chaturbhuj, Monatsh. Chem. 148, 1463 (2017)

    Article  CAS  Google Scholar 

  51. C.K. Khatri, M.S. Patil, G.U. Chaturbhuj, J. Iran. Chem. Soc. 14, 1683 (2017)

    Article  CAS  Google Scholar 

  52. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 2144 (2017)

    Article  CAS  Google Scholar 

  53. M.S. Patil, A.V. Palav, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58, 2859 (2017)

    Article  CAS  Google Scholar 

  54. M.S. Patil, C. Mudaliar, G.U. Chaturbhuj, Tetrahedron Lett. 58, 3256 (2017)

    Article  CAS  Google Scholar 

  55. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Monatsh. Chem. (2017). doi:10.1007/s00706-017-2013-x

    Google Scholar 

  56. M. Hong, G. Xiao, J. Fluor. Chem. 146, 11 (2013)

    Article  CAS  Google Scholar 

  57. G.W. Gribble, F.P. Bousquet, Tetrahedron 27, 3785 (1971)

    Article  CAS  Google Scholar 

  58. Z. Wang, M. Lu, RSC Adv. 4, 1234 (2014)

    Article  CAS  Google Scholar 

  59. K.B. Muchowska, C. Adam, I.K. Mati, S.L. Cockroft, J. Am. Chem. Soc. 135, 9976 (2013)

    Article  CAS  Google Scholar 

  60. G. Kobayashi, T. Saito, Y. Kitano, Synthesis (Stuttg) 2011, 3225 (2011)

    Article  Google Scholar 

  61. D. Habibi, H. Sahebekhtiari, M. Nasrollahzadeh, A. Taghipour, Lett. Org. Chem. 10, 209 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to University Grants Commission (UGC), India, for their financial support.

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Correspondence to Ganesh U. Chaturbhuj.

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Khatri, C.K., Chaturbhuj, G.U. Sulfated polyborate-catalyzed N-formylation of amines: a rapid, green and efficient protocol. J IRAN CHEM SOC 14, 2513–2519 (2017). https://doi.org/10.1007/s13738-017-1186-x

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  • DOI: https://doi.org/10.1007/s13738-017-1186-x

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