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Pentafluorophenylammonium triflate (PFPAT): A new organocatalyst for the one-pot three-component synthesis of α-aminophosphonates

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Abstract

In the presence of a catalytic amount of pentafluorophenylammonium triflate (10 mol %), dimethyl phosphite reacts with imines (generated in situ from aldehydes and amines) to yield the corresponding coupling products in good yield. The organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.

α-Aminophosphonate derivatives were synthesized in excellent yield using PFPAT as an efficient organocatalyst.

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References

  1. Bartlett P A, Hanson J E and Giannousis P P 1990 J. Org. Chem. 55 6268

    Article  CAS  Google Scholar 

  2. Kafarski P and Lejczak B 1991 Phosphorus Sulfur Silicon Relat. Elem. 63 193

    Article  CAS  Google Scholar 

  3. Allen M C, Fuhrer W, Tuck B, Wade R and Wood J M 1989 J. Med. Chem. 32 1652

    Article  CAS  Google Scholar 

  4. Logusch E W, Walker D M, McDonald J F, Leo G C and Franz J E 1988 J. Org. Chem. 53 4069

    Article  CAS  Google Scholar 

  5. Giannousis P P and Bartlett P A 1987 J. Med. Chem. 30 1603

    Article  CAS  Google Scholar 

  6. Peyman A, Budt K H, Spanig J, Stowasser B and Ruppert D 1992 Tetrahedron Lett. 33 4549

    Article  CAS  Google Scholar 

  7. Stowasser B, Budt K H, Jian-Qi I, Peyman A and Ruppert D 1992 Tetrahedron Lett. 33 6625

    Article  CAS  Google Scholar 

  8. Natchev I A 1988 Liebigs Ann. Chem. 861

  9. Emsley J and Hall D 1976The chemistry of phosphorus. Harper and Row, London, p 494

    Google Scholar 

  10. Maier L and Spörri H 1991 Phosphorus Sulfur Silicon Relat. Elem. 61 69

    Article  CAS  Google Scholar 

  11. Huang J and Chen R 2000 Heteroatom Chem. 11 480

    Article  CAS  Google Scholar 

  12. Smith A B, Taylor C M, Benkovic S J and Hirschmann R 1994 Tetrahedron Lett. 35 6853

    Article  CAS  Google Scholar 

  13. Kim D Y and Yong Rhie D 1997 Tetrahedron 53 13603

    Article  CAS  Google Scholar 

  14. Afarinkia K, Cadogan J I G and Rees C W 1990 Synlett 415

  15. Yuan C, Chen S and Wang G 1991 Synthesis 490

  16. Sasai H, Shigeru A, Tahara Y and Shibasaki M 1995 J. Org. Chem. 60 6656

    Article  CAS  Google Scholar 

  17. Laschat S and Kunz H 1992 Synthesis 90

  18. Manjula A, Vittal R B and Parvathi N 2003 Synth. Commun. 33 2963

    Article  CAS  Google Scholar 

  19. Genet J P, Uziel J, Port M, Touzin S, Roland A M, Thorimbert S and Tanier S 1992 Tetrahedron Lett. 33 77

    Article  CAS  Google Scholar 

  20. Laschat S and Kunz H 1992 Synthesis 90

  21. Pudovik A N 1952Dokl. Akad. Nauk SSSR 83 865; 1953 Chem. Abstr. 47 4300

  22. Petrov K A, Chauzov V A and Erkhina T S 1974Usp. Khim. 43 2045; 1975 Chem. Abstr. 82 449

  23. Manjula A, Rao V and Neelakanthan P 2003 Synth. Commun. 33 2963

    Article  CAS  Google Scholar 

  24. Yadav J S, Reddy B V S, Raj S, Reddy K B and Prasad A R 2001 Synthesis 22

  25. Zon J 1981 Pol. J. Chem. 55 643

    CAS  Google Scholar 

  26. Ha H J and Nam G S 1992 Synth. Commun. 22 1143

    Article  CAS  Google Scholar 

  27. Heydari A, Hamadi H and Pourayoubi M 2007 Catal. Commun. 8 1224

    Article  CAS  Google Scholar 

  28. Bhagat S and Chakraborti A K 2007 J. Org. Chem. 72 1263

    Article  CAS  Google Scholar 

  29. Heydari A and Arefi A 2007 Catal. Commun. 8 1023

    Article  CAS  Google Scholar 

  30. Bhattacharya A K and Kaur T 2007 Synlett 745

  31. Qian C and Huang T 1998 J. Org. Chem. 63 4125

    Article  CAS  Google Scholar 

  32. Ranu B C, Hajra A and Jana J 1999 Org. Lett. 1 1141

    Article  CAS  Google Scholar 

  33. Firouzabadi H, Iranpoor N and Sobhani S 2004 Synthesis 2692

  34. Heydari A, Karimian A and Ipaktschi J 1998 Tetrahedron Lett. 39 6729

    Article  CAS  Google Scholar 

  35. Kaboudin B and Nazari R 2001 Tetrahedron Lett. 42 8211

    Article  CAS  Google Scholar 

  36. Akiyama T, Sanada M and Fuchibe K 2003 Synlett 1463

  37. Yadav J S, Reddy B V S and Madan C 2001 Synlett 1131

  38. Kudrimoti S and Bommena Roa V 2005 Tetrahedron Lett. 46 1209

    Article  CAS  Google Scholar 

  39. Qian C and Huang T 1998 J. Org. Chem. 63 4125

    Article  CAS  Google Scholar 

  40. Ranu B C, Hajra A and Jana U 1999 Org. Lett. 1 1141

    Article  CAS  Google Scholar 

  41. Chandrasekhar S, Prakash S J, Jagadeswar V and Narsihmulu C 2001 Tetrahedron Lett. 42 5561

    Article  CAS  Google Scholar 

  42. Vahdat S M, Baharfar R, Tajbakhsh M, Heydari A, Baghbanian S M and Khaksar S 2008 Tetrahedron Lett. 49 6501

    Article  CAS  Google Scholar 

  43. Heydari A, Khaksar S and Tajbakhsh M 2009 Tetrahedron Lett. 50 77

    Article  CAS  Google Scholar 

  44. Hazeri N, Maghsoodlou M T, Habibi-Khorassani S M, Aboonajmi J, Lashkari M and Sajadikhah S S 2014 Res. Chem. Intermed. 40 1781

    Article  CAS  Google Scholar 

  45. List B 2007 Chem. Rev. 107 5413

    Article  CAS  Google Scholar 

  46. Schreiner P R 2003 Chem. Soc. Rev. 32 289

    Article  CAS  Google Scholar 

  47. Doyle A G and Jacobsen E N 2007 Chem. Rev. 107 5713

    Article  CAS  Google Scholar 

  48. Dalko P I and Moisan L 2004 Angew. Chem., Int. Ed. 43 5138

    Article  CAS  Google Scholar 

  49. Funatomi T, Wakasugi K, Misaki T and Tanabe Y 2006 Green Chem. 8 1022

    Article  CAS  Google Scholar 

  50. Iida A, Osada J, Nagase R, Misaki T and Tanabe Y 2007 Org. Lett. 9 1859

    Article  CAS  Google Scholar 

  51. Nagase R, Osada J, Tamagaki H and Tanabe Y 2010 Adv. Synth. Catal. 352 1128

    Article  CAS  Google Scholar 

  52. Khaksar S, Vahdat S M and Rezaee F 2013 C R Chim. 16 144

    Article  CAS  Google Scholar 

  53. Khaksar S and Behzadi N 2012 Comb. Chem. High T. Scr. 15 845

    CAS  Google Scholar 

  54. Khaksar S and Ostad S M 2011 J. Fluorine Chem. 132 937

    Article  CAS  Google Scholar 

  55. Khaksar S, Fattahi E and Fattahi E 2011 Tetrahedron Lett. 52 5943

    Article  CAS  Google Scholar 

  56. Khaksar S, Vahdat S M and Moghaddamnejad R N 2012 Monatsh. Chem. 143 1671

    Article  CAS  Google Scholar 

  57. Khaksar S, Vahdat S M, Tajbakhsh M, Jahani F and Heydari A 2010 Tetrahedron Lett. 51 6388

    Article  CAS  Google Scholar 

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Acknowledgement

This research is supported by the Islamic Azad University, Ayatollah Amoli Branch.

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Correspondence to SAMAD KHAKSAR.

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Supplementary data associated with this article synthesis and NMR spectra can be found in the online version ( www.ias.ac.in/chemsci).

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MALAMIRI, F., KHAKSAR, S. Pentafluorophenylammonium triflate (PFPAT): A new organocatalyst for the one-pot three-component synthesis of α-aminophosphonates. J Chem Sci 126, 807–811 (2014). https://doi.org/10.1007/s12039-014-0636-6

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  • DOI: https://doi.org/10.1007/s12039-014-0636-6

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