Monatshefte für Chemie / Chemical Monthly

, Volume 136, Issue 9, pp 1583–1589 | Cite as

CsF-Celite, an Efficient Solid State Reagent for the Syntheses of Thioesters and Thioethers

  • Syed T. A. Shah
  • Khalid M. Khan
  • Hidayat Hussain
  • Safdar Hayat
  • Wolfgang Voelter
Article

Summary.

Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters.

Keywords. Cesium fluoride-Celite, Thioethers, Thioesters. 

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References

  1. Lee, JC, Choi, Y 1998Synth Commun282021Google Scholar
  2. Khan, KM, Hayat, S, Zia-Ullah, , Atta-ur-Rahman, , Choudhary, MI, Maharvi, GM, Bayer, E 2003Synth Commun333435CrossRefGoogle Scholar
  3. Hayat, S, Atta-ur-Rahman, , Choudhary, MI, Khan, KM, Schumann, W, Bayer, E 2001Tetrahedron579951CrossRefGoogle Scholar
  4. Vivek, P, Kaushik, MP 2004Catalysis Commun5515CrossRefGoogle Scholar
  5. Clark, JH, Holland, HL, Miller, JM 1976Tetrahedron Lett383361CrossRefGoogle Scholar
  6. Clark, JH, Miller, JM 1977Tetrahedron Lett7599CrossRefGoogle Scholar
  7. Clark, JH, Miller, JM 1977J Am Chem Soc99498CrossRefGoogle Scholar
  8. Clark JH, Miller JM (1977) J Chem Soc Perkin Trans 1, 2063Google Scholar
  9. Clark JH, Miller JM (1976) J Chem Soc Chem Commun 229Google Scholar
  10. Clark JH, Miller JM (1977) J Chem Soc Chem Commun 64Google Scholar
  11. Miller JM, So K-H, Clark JH (1978) J Chem Soc Chem Commun 466Google Scholar
  12. Clark JH (1978) J Chem Soc Chem Commun 789Google Scholar
  13. Yamada, M, Yahiro, S, Yamano, T, Nakatani, Y, Ourisson, G 1990Bull Soc Chim Fr127824Google Scholar
  14. Kruizinga, WH, Kellogg, RM 1981J Am Chem Soc1035183CrossRefGoogle Scholar
  15. Yang, W, Drueckhammer, DG 2001J Am Chem Soc12311004CrossRefPubMedGoogle Scholar
  16. Peach ME (1974) In: Patai S (ed) The Chemistry of the Thiol Groups. Wiley, London, p 721Google Scholar
  17. Goux, C, Lhoste, P, Sinou, D 1992Tetrahedron Lett338099CrossRefGoogle Scholar
  18. Herriott, AW, Picker, D 1975J Am Chem Soc972345CrossRefGoogle Scholar
  19. Page, PCB, Klair, SS, Brown, MP, Harding, MM, Smith, CS, Maginn, SJ, Mulley, S 1988Tetrahedron Lett294477CrossRefGoogle Scholar
  20. Li, C-J, Harpp, DN 1992Tetrahedron Lett337293CrossRefGoogle Scholar
  21. Kosugi, M, Ogata, T, Terada, M, Sano, H, Migita, T 1985Bull Chem Soc Jpn583657Google Scholar
  22. Toste, FD, Still, IWJ 1995Tetrahedron Lett364361CrossRefGoogle Scholar
  23. Toste, FD, Laronde, F, Still, IWJ 1995Tetrahedron Lett362949CrossRefGoogle Scholar
  24. (a) Harpp DN, Gingras M (1988) J Am Chem Soc 110: 7737; (b) Gingras M, Chan TH, Harpp DN (1990) J Org Chem 55: 2078Google Scholar
  25. Li T-S, Li A-X (1998) J Chem Soc Perkin Trans 1, 1913Google Scholar
  26. Richter, LS, Marsters, JC,Jr, Gadek, TR 1994Tetrahedron Lett351631CrossRefGoogle Scholar
  27. Yin, J, Pidgeon, C 1997Tetrahedron Lett385953CrossRefGoogle Scholar
  28. Shah STA, Khan KM, Fecker M, Voelter W (2003) Tetrahedron Lett 44: 6789; b) Shah STA, Khan KM, Heinrich AM, Choudhary MI, Voelter W (2002) Tetrahedron Lett 43: 8603Google Scholar
  29. Karasch, MS, Fuchs, CF 1948J Org Chem1397CrossRefGoogle Scholar
  30. Büchi, J, Prost, M, Eichenberger, H, Leiberherr, R 1952Helv Chem Acta351527CrossRefGoogle Scholar
  31. Drabowicz J, Mikolajczyk M (1978) Synthesis 542Google Scholar
  32. Drabowicz J, Mikolajczyk M (1976) Synthesis 527Google Scholar
  33. Harayama, H, Nagahama, T, Kozera, T, Kimura, M, Fugami, K, Tanaka, S, Tamaru, Y 1997Bull Chem Soc Jpn70445Google Scholar
  34. Cogolli, P, Testaferri, L, Tingoli, M, Tiecco, M 1979J Org Chem442636CrossRefGoogle Scholar
  35. a) Foster DG, Reid EE (1924) J Am Chem Soc 46: 1936; b) Pasto DJ, Cottard F, Jumelle L (1994) J Am Chem Soc 116: 8978Google Scholar
  36. Lapkin, II, Bogoslovskii, NV, Mozhova, NF 1966Chem Abstr6411115dGoogle Scholar
  37. Cranham, JE, Greenwood, D, Stevenson, HA 1958J Sci Food Agric9147Google Scholar
  38. Maekawa, K, Narasaka, K, Mukaiyama, T 1973Bull Chem Soc Jpn463478Google Scholar
  39. Fujita E, Nagao Y, Seno K, Takao S, Miyasaka T, Kimura M, Watson WH (1981) J Chem Soc Perkin Trans 1, 914Google Scholar
  40. Cilento, G 1953J Am Chem Soc753748CrossRefGoogle Scholar
  41. Morgenstern, J, Mayer, R 1968Z Chem8146Google Scholar
  42. (a) Sheehan JC, Beck CW (1955) J Am Chem Soc 77: 4875; (b) Cilento G, Walter WF (1954) J Am Chem Soc 76: 4469Google Scholar
  43. Pelster H, Hahn W, Goliasch K, Behrenz W (December 16, 1965) Farbenfabriken Bayer A-G, Patent No Ger-1,207,140; Chem Abstr (1966) 64: 6573bGoogle Scholar
  44. Gulevich, YV, Bumagin, NA, Beletskaya, IP 1988J Org Chem (USSR)241918Google Scholar

Copyright information

© Springer-Verlag/Wien 2005

Authors and Affiliations

  • Syed T. A. Shah
    • 1
  • Khalid M. Khan
    • 2
  • Hidayat Hussain
    • 2
  • Safdar Hayat
    • 2
  • Wolfgang Voelter
    • 1
  1. 1.Abteilung für Physikalische Biochemie des Physiologisch-chemischen Instituts der Universität TübingenTübingenGermany
  2. 2.HEJ Research Institute of Chemistry, International Center for Chemical Sciences, University of KarachiKarachiPakistan

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