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A green and highly efficient alkylation of thiols in water

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Abstract

An environmentally benign and efficient process for the preparation of thioethers was developed by simple and practical reactions of alkyl halides and thiols in water in the presence of K2CO3 or Et3N in very high yields. The reaction of aryl, alkyl, aliphatic and hindered thiols with various alkyl halides gave the corresponding products with significant advantages such as high conversions, short reaction time, mild reaction conditions, and low cost, simple workup with good to quantitative yields.

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References

  1. C.-J. Li, Chem. Rev. 105 (2005) 3095

    CAS  Google Scholar 

  2. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Chem. Commun. (2005) 789

    Google Scholar 

  3. M.C. Pirrung, K.D. Sarma, J. Am. Chem. Soc. 126 (2004) 444

    CAS  Google Scholar 

  4. H. Firouzabadia, N. Iranpoor, H. Alinezhad, J. Iran. Chem. Soc. 6 (2009) 177

    Google Scholar 

  5. A.A. Jafari, F. Moradgholi, F. Tamaddon, J. Iran. Chem. Soc. 6 (2009) 588

    CAS  Google Scholar 

  6. H. Zali Boeini, J. Iran. Chem. Soc. 6 (2009) 547

    Google Scholar 

  7. M. Bararjanian, S. Balalaie, B. Movassagh, A.M. Amani, J. Iran. Chem. Soc. 6 (2009) 436

    CAS  Google Scholar 

  8. N. Azizi, E. Akbari, M.R. Saidi, J. Iran. Chem. Soc. 6 (2009) 165.

    CAS  Google Scholar 

  9. H. Firouzabadi, A. Jamalian, J. Sulfur Chem. 28 (2007) 631

    Google Scholar 

  10. R.J. Cremlyn, Introduction to Organo-Sulfur Chemistry, Wiley & Sons, New York, 1996

    Google Scholar 

  11. M.D. McReynolds, J.M. Doughtery, P.R. Hanson, Chem. Rev. 104 (2004) 2239.

    CAS  Google Scholar 

  12. J.Y. Hwang, Y.-D. Gong, J. Comb. Chem. 8 (2006) 297.

    CAS  Google Scholar 

  13. G. Solladie, Synthesis (1981) 185

    Google Scholar 

  14. G.H. Posner, in: S. Patai, Z. Rappoport, C.J.M. Sterling (Eds.), The Chemistry of Sulfones and Sulfoxides, Chap. 16, Wiley, Chichester, 1988, pp. 823–849.

    Google Scholar 

  15. L.Y. Goh, M.E. Teo, S.B. Khoo, W.K. Leong, J.J. Vittal, J. Organomet. Chem. 664 (2002) 161

    CAS  Google Scholar 

  16. C.A. Christensen, M. Meldal, J. Comb. Chem. 9 (2007) 79.

    CAS  Google Scholar 

  17. R.N. Salvatore, R.A. Smith, A.K. Nischwitz T. Gavin, Tetrahedron Lett. 46 (2005) 8931; au[b)_S. Patai, The Chemistry of the Functional Groups-The Chemistry of the Thiol Group, Wiley, London, UK, 1974, p. 669

    Google Scholar 

  18. J.F. Boscato, J.M. Catala, E. Franta, J. Brossas, Tetrahedron Lett. 21 (1980) 1519

    CAS  Google Scholar 

  19. F.J.A. Hundscheid, V.K. Tandon, P.H.A.M. Rouwette, A.M. Van Leusen, Tetrahedron 43 (1987) 5073

    CAS  Google Scholar 

  20. J. Malmstrom, V. Gupta, L. Engman, J. Org. Chem. 63 (1998) 3318

    Google Scholar 

  21. P. Blanchard, B. Jousselme, P. Frere, J. Roncali, J. Org. Chem. 67 (2002) 3961

    CAS  Google Scholar 

  22. D. Landini, F. Rolla, Synthesis (1974) 496

    Google Scholar 

  23. J.M. Khurana, P.K. Sahoo, Synth. Commun. 22 (1992) 1691

    CAS  Google Scholar 

  24. P.C. Herradura, K.A. Pendola, R.K. Guy, Org. Lett. 2 (2000) 2019

    CAS  Google Scholar 

  25. N. Taniguchi, J. Org. Chem. 69 (2004) 6904

    CAS  Google Scholar 

  26. M.T. Martin, A.M. Thomas, D.G. York, Tetrahedron Lett. 43 (2002) 2145

    CAS  Google Scholar 

  27. N.A. Sasaki, C. Hashimoto, P. Potier, Tetrahedron Lett. 28 (1987) 6069.

    CAS  Google Scholar 

  28. D.P. Curran, In Comprehensive Organic Synthesis, Vol. 4

  29. H. Firouzabadi, M. Jafarpour, J. Iran. Chem. Soc. 5 (2008) 159

    CAS  Google Scholar 

  30. B.M. Trost, I. Fleming (Eds.), Pergamon, New York, 715 (1991)

  31. K. Griesbaum, Angew. Chem., Int. Ed. Engl. 9 (1970) 273

    CAS  Google Scholar 

  32. C.G. Screttas, M.J. Micha-Screttas, J. Org. Chem. 44 (1979) 713

    CAS  Google Scholar 

  33. M. Belley, R. Zamboni, J. Org. Chem. 54 (1989) 1230

    CAS  Google Scholar 

  34. P. Kumar, R.K. Pandey, V.R. Hegde, Synlett (1999) 1921

    Google Scholar 

  35. S. Kanagasabathy, A. Sudalai, B.C. Benicewicz, Tetrahedron Lett. 42 (2001) 3791.

    Google Scholar 

  36. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Synlett (2005) 299

    Google Scholar 

  37. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Cat. 347 (2005) 655

    CAS  Google Scholar 

  38. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A.M. Ghaderi, J. Mol. Catal. A. Chem. 249 (2006) 98

    CAS  Google Scholar 

  39. G.L. Khatik, R. Kumar, A.K. Chakraborti, Org. Lett. 8 (2006) 2433.

    CAS  Google Scholar 

  40. H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Mol. Cat. A: Chem. 250 (2006) 237

    CAS  Google Scholar 

  41. F. Fringuelli, F. Pizzo, S. Tortoioli, L. Vaccaro, Adv. Synth. Catal. 344 (2002) 379

    CAS  Google Scholar 

  42. B.P. Bandgar, A.V. Patil, O.S. Chavan, V.T. Kamble, Catal. Commun. 8 (2007) 1065.

    CAS  Google Scholar 

  43. B.C. Ranu, T. Mandal, Tetrahedron Lett. 47 (2006) 6911

    CAS  Google Scholar 

  44. B.C. Ranu, T. Mandal, Synlett (2007) 925

    Google Scholar 

  45. B.C. Ranu, R. Jana, Adv. Synth. Catal. 347 (2005) 1811

    CAS  Google Scholar 

  46. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 47 (2006) 93

    CAS  Google Scholar 

  47. H. Firouzabadi, N. Iranpoor, M. Jafarpour, J. Sulfur Chem. 26 (2005) 313

    CAS  Google Scholar 

  48. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Tetrahedron Lett. 46 (2005) 2683.

    CAS  Google Scholar 

  49. N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M.R. Saidi, J. Org. Chem. 71 (2006) 3634

    CAS  Google Scholar 

  50. N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8 (2006) 2079

    CAS  Google Scholar 

  51. N. Azizi, M.R. Saidi, Org. Lett. 7 (2005) 3649

    CAS  Google Scholar 

  52. N. Azizi, M.R. Saidi, Tetrahedron 63 (2007) 888

    CAS  Google Scholar 

  53. N. Azizi, F. Aryanasab, M.R. Saidi, Org. Biomol. Chem. (2006) 4275.

    Google Scholar 

  54. N. Azizi, M.R. Saidi, Organometallics 23 (2004) 1457

    CAS  Google Scholar 

  55. N. Azizi, M.R. Saidi, Tetrahedron 60 (2004) 383

    CAS  Google Scholar 

  56. N. Azizi, F. Rajabi, M.R. Saidi, Tetrahedron Lett. 45 (2004) 9233

    CAS  Google Scholar 

  57. B. Mirmashhori, N. Azizi, M.R. Saidi, J. Mole. Catal. A: Chem. 247 (2006) 159

    CAS  Google Scholar 

  58. N. Azizi, R. Yousefi, M.R. Saidi, J. Organomet. Chem. 691 (2006) 817

    CAS  Google Scholar 

  59. N. Azizi, M.R. Saidi, Catal. Commun. 7 (2006) 224

    CAS  Google Scholar 

  60. N. Azizi, F. Aryanasab, M.R. Saidi, Synlett (2007) 1239.

    Google Scholar 

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Azizi, N., Khajeh Amiri, A., Bolourtchian, M. et al. A green and highly efficient alkylation of thiols in water. JICS 6, 749–753 (2009). https://doi.org/10.1007/BF03246165

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  • DOI: https://doi.org/10.1007/BF03246165

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