Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser’s reagent

Abstract

A facile synthesis of substituted diaryliodonium tosylates (toluene-p-sulfonates) was developed, based on the treatment of substituted aryltributylstannanes with Koser’s reagent [hydroxy(tosyloxy)iodobenzene]. In this manner, several new diaryliodonium salts, bearing one or more substituents on one aryl ring, were prepared in useful yields under mild conditions (dichloromethane, room temperature, 2 h).

References

1. G. F. Koser, in The Chemistry of Functional Groups, Supplement D, Eds. S. Patai and Z. Rappoport, Wiley, New York, 1983, ch. 25.
2. G. A. Olah, Halonium Ions, Wiley, New York, 1975.
3. V. V. Grushin, Acc. Chem. Res., 1992, 25, 529.
4. P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274.
5. A. Vargolis, Hypervalent Iodine in Organic Synthesis, Academic Press, 1996.
6. F. M. Beringer, M. Drexler, E. M. Gindler and C. C. Lumpkin, J. Am. Chem. Soc., 1953, 75, 2705.
7. F. M. Beringer, A. Briedley, M. Drexler, E. M. Gindler and C. C. Lumpkin, J. Am. Chem. Soc., 1953, 75, 2708.
8. M. Van der Puy, J. Fluorine Chem., 1982, 21, 385.
9. J. V. Crivello, Adv. Polym. Sci., 1984, 62, 1.
10. V. W. Pike and F. I. Aigbirhio, J. Chem. Soc., Chem. Commun., 1995, 2215.
11. V. W. Pike and F. I. Aigbirhio, J. Labelled Compd. Radiopharm., 1995, 37, 120.
12. A. Shah, V. W. Pike and D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1, 1998, 2043.
13. M. E. Phelps, J. Mazziotta and H. Schelbert, Positron Emission Tomography and Autoradiography; Principles and Applications for the Brain and Heart, Raven Press, New York, 1986.
14. A. J. Palmer, J. C. Clark and R. W. Goulding, Radiopharmaceuticals and Other Compounds Labelled with Short-lived Radionuclides, Pergamon Press, New York, 1977.
15. T. Guddat, W. Herdering, A. Knochel, H. Salehi and O. Zwernemann, J. Labelled Compd. Radiopharm., 1989, 26, 5.
16. J. S. Ng, J. A. Katzenellenbogen and M. R. Kilbourn, J. Org. Chem., 1981, 46, 2520.
17. D. A. Widdowson and M. N. Rosenfeld, J. Chem. Soc., Chem. Commun., 1979, 914.
18. T. J. Tewson and M. J. Welch, J. Chem. Soc., Chem. Commun., 1979, 1149.
19. A. Shah, V. W. Pike and D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1, 1997, 2463.
20. P. Kazmierczak and L. Skulski, Synthesis, 1995, 1027.
21. N. S. Zefirov, T. M. Kasumov, A. S. Koz'min, V. D. Sorokin, P. J. Stang and V. V. Zhdankin, Synthesis, 1993, 1209.
22. T. Kitamura, J. Matsuyaki and H. Taniguchi, Synthesis, 1994, 147.
23. G. F. Koser, R. H. Wettach and C. S. Smith, J. Org. Chem., 1980, 45, 1543.
24. O. Neiland and B. Karele, J. Org. Chem. USSR (Engl. Transl.), 1970, 6, 889.
25. G. F. Koser and R. H. Wettach, J. Org. Chem., 1980, 45, 1542.
26. G. F. Koser, R. H. Wettach, J. M. Troup and B. A. Frenz, J. Org. Chem., 1976, 41, 3609.
27. G. Picher and H. A. Skinner, The Chemistry of the Metal-Carbon Bond, eds. F. R. Hartley and S. Patai, Wiley, New York, 1982, p. 43.
28. T. L. Cottrell, The Strengths of Chemical Bonds, Butterworths, London, 1958, 2nd edn.
29. H. Azizian, C. Eaborn and A. Pidcock, J. Organomet. Chem., 1981, 215, 49.
30. C. Eaborn and G. Seconni, J. Chem. Soc., Perkin Trans. 2, 1976, 925.
31. H. Ali and J. E. van Lier, Synthesis, 1996, 423.
32. A. R. Katritzky, J. K. Gallos and H. D. Durst, Magn. Reson. Chem., 1989, 27, 815.
33. D. F. Ewing, Magn. Reson. Chem., 1979, 12, 499.
34. P. J. Stang, V. V. Zhdankin, R. Tykwinski and N. S. Zefirov, Tetrahedron Lett., 1992, 33, 1419.
35. F. M. Beringer, R. A. Falk, M. Karniol, I. Lillien, G. Masullo, M. Mausner and E. Sommer, J. Am. Chem. Soc., 1959, 81, 342.
36. M. C. Caserio, D. L. Glusker and J. D. Roberts, J. Am. Chem. Soc., 1959, 81, 336.