Indium-mediated Coupling Reaction of Sulfonyl Chlorides with Alkyl Bromides in Water. A Facile Synthesis of Sulfones

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Lei Wang and Yongmin Zhang


Abstract

Indium-mediated coupling of alkyl bromides with aromatic sulfonyl chlorides gives the corresponding sulfones in aqueous media with moderate to good yields.


References

  1. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207 CrossRef CAS; C. J. Li, Chem. Rev., 1993, 93, 2023 CrossRef CAS; A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741 CrossRef CAS; C. J. Li, Tetrahedron, 1996, 52, 5643 CrossRef CAS.
  2. L. A. Paquette and T. M. Mitzel, J. Am. Chem. Soc., 1996, 118, 1931 CrossRef CAS; L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917 CrossRef CAS; C. J. Li, D. L. Chen, Y. Q. Lu, J. X. Haberman and J. T. Mague, J. Am. Chem. Soc., 1996, 118, 4216 CrossRef CAS.
  3. C. J. Li and T. H. Chan, Tetrahedron Lett., 1991, 32, 7071; T. H. Chan and M. B. Isaac, Pure Appl. Chem., 1996, 68, 919 CrossRef CAS.
  4. T. H. Chan and C. J. Li, J. Chem. Soc., Chem. Commun., 1992, 747 RSC; D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 58, 7937 CrossRef CAS; M. B. Isaac and T. H. Chan, J. Chem. Soc., Chem. Commun., 1995, 1003 RSC; T. H. Chan and M. C. Lee, J. Org. Chem., 1995, 60, 4228 CrossRef CAS.
  5. N. S. Simpkins, Sulfones in Organic Synthesis, in Tetrahedron Organic Chemistry Series Vol. 10, ed. J. E. Baldwin and P. D. Magnus, Pergamon, Oxford, 1993 Search PubMed; S. Patai, Z. Rappoport and C. Stirling, The Chemistry of Sulfones and Sulfoxides, Wiley, New York, 1988 Search PubMed.
  6. E. Block, in The Chemistry of Functional Groups, Supplement E, Part 1, ed. S. Patai, Wiley, New York, 1980, ch. 13 Search PubMed; J. Smeek and J. S. Fowler, J. Org. Chem., 1968, 33, 3422 Search PubMed.
  7. G. E. Vennstra and B. Zwaneburg, Synthesis, 1975, 519 CrossRef CAS.
  8. P. Sun, L. Wang and Y. Zhang, Tetrahedron Lett., 1997, 38, 5549 CrossRef CAS.
  9. K. Tsuboyama, K. Takeda, K. Torii and H. Ogura, Chem. Pharm. Bull., 1990, 38, 2357 CAS.
  10. J. P. Weidner and S. S. Block, Synthesis, 1970, 583 CrossRef CAS.
  11. J. Wildeman and A. M. Leusen, Synthesis, 1979, 733 CrossRef CAS.
  12. Beilstein, VI, 1923, p. 299 Search PubMed.
  13. B. M. Trost and R. Braslau, J. Org. Chem., 1988, 53, 532 CrossRef CAS.
  14. J. Tröger and O. Beck, J. Prakt. Chem., 1913, 87, 295.
  15. R. T. Amel and P. T. Marek, J. Org. Chem., 1973, 38, 3513 CAS.
  16. R. Otto, J. Prakt. Chem., 1884, 30, 343 Search PubMed.
  17. R. L. Shriner, H. C. Struck and W. J. Jorison, J. Am. Chem. Soc., 1930, 52, 2069.
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