Pronounced catalytic effect of micellar solution of sodium dodecyl sulfate (SDS) for regioselective iodination of aromatic compounds with a sodium iodide/cerium(IV) trihydroxide hydroperoxide system

Advanced Synthesis and Catalysis

Volumn 347, Issue 15, 2005, Pages 1925-1928

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Garzan, Atefeh ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Aromatic compounds; Cerium(IV) trihydroxide hydroperoxide; Iodination; Sodium dodecyl sulfate; Sodium iodide

Indexed keywords

EID: 29144482917     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505222     Document Type: Article

References (47)

1. P. T. Anastas, T. C. Williamson, (Eds.), Green Chemistry, ACS Symposium Series 626, American Chemical Society, Washington DC, 1996, and references cited therein.
2. a) P. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998;
3. b) P. Tundo, P. Anastas, D. StC. Black, J. Breen, T. Collins, S. Memoli, J. Miyamoto, M. Poliakoff, W. Tumas, Pure Appl. Chem. 2000, 72, 1207.
4. a) P. A. Grieco, (Ed.), Organic Synthesis in Water, Blacky Academic and Professional, London, 1998;
5. b) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997;
6. c) B. Cornils, W. A. Herrmann, Aqueous-Phase Organometallic Chemistry: Concepts and Applications, Wiley-VCH, Weinheim, 1998.
7. a) D. C. Rideout, R. Breslow, J. Am. Chem. Soc. 1980, 102, 7816;
8. b) R. Breslow, Acc. Chem. Res. 1991, 24, 159;
9. c) J. B. F. N. Engberts, M. Blandamer, Chem. Commun. 2001, 1701.
10. a) J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, London, 1975;
11. b) Mixed Surfactant Systems, (Eds.: P. M. Holland, D. N. Rubingh), American Chemical Society, Washington, DC, 1992;
12. c) Structure and Reactivity in Aqueous Solution, (Eds.: C. J. Cramer, D. G. Truhlar), American Chemical Society, Washington, DC, 1994;
13. d) Surfactant-Enhanced Subsurface Remediation, (Eds.: D. A. Sabatini, R. C. Knox, J. H. Harwell), American Chemical Society, Washington, DC, 1994;
14. e) K. Manabe, X. M. Sun, S. Kobayashi, J. Am. Chem. Soc. 2001, 123, 10101.
15. a) I. V. Berezin, K. Martinek, A. K. Yatsimirskii, Russ. Chem. Rev. 1973, 42, 787;
16. b) S. Tałcioglu, Tetrahedron 1996, 52, 11113.
17. a) F. M. Menger, J. U. Rhee, H. K. Rhee, J. Org. Chem. 1975, 40, 3803;
18. b) C. Larpent, E. Bernard, F. B. Menn, H. Patin, J. Mol. Catal. A: Chem. 1997, 116, 277;
19. c) T. Dwars, U. Schmidt, C. Fischer, I. Grassert, R. Kempe, R. FrÖhlich, K. Drauz, G. Öehme, Angew. Chem. Int. Ed. 1998, 37, 2851;
20. d) I. Grassert, U. Schmidt, S. Ziegler, C. Fischer, G. Oehme, Tetrahedron: Asymmetry 1998, 9, 4193;
21. e) R. Selke, J. Hölz, A. Riepe, A. Borner, Chem. Eur. J. 1998, 4, 769;
22. f) K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 5593;
23. g) K. Yonehara, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9381;
24. h) M. S. Goedheijt, B. E. Hanson, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2000, 122, 1650.
25. N. Iranpoor, H. Firouzabadi, M. Shekarrize, Org. Biomol. Chem. 2003, 724.
26. H. Firouzabadi, N. Iranpoor, A. A. Jafari, Adv. Synth. Catal. 2005, 347, 655.
27. Y. Sasson, Formation of Carbon-Halogen Bonds (Cl, Br, I), in: The Chemistry of Halides, Pseudo-Halides, and Azides, Supplement D1, (Ed.: S. Patai, Z. Rappoport), Wiley-Interscience, Chichester, 1995, pp. 535-620.
28. E. B. Merkushev, Synthesis 1988, 923.
29. a) B. Abderrazak, F. Francisco, Y. Miguel, Tetrahedron 1994, 50, 5139;
30. b) G. A. Olah, W. Qi, G. Sandford, G. K. Prakash, J. Org. Chem. 1993, 58, 3194.
31. th edn., Wiley-interscience, New York, 2000.
32. B. Krassowska-Swiebocka, P. Lulinski, L. Skulski, Synthesis 1995, 926.
33. A. Himizu, K. Yamataka, T. Isoya, Bull. Chem. Soc. Jpn. 1985, 58, 1611.
34. a) V. K. Chaikovskii, A. N. Novikov, Zh. Prikl. Khim. 1984, 57, 134;
35. b) V. K. Chaikovskii, V. T. Novikov, A. N. Novikov, F. S. Garifullina, Zh. Obshch. Khim. 1985, 55, 893.
36. a) H. O. Wirth, O. Königstein, W. Kern, Liebigs Ann. Chem. 1977, 42, 4049;
37. b) S. Ahmed, S. Razaq, Tetrahedron 1976, 32, 503.
38. a) H. Suzuki, K. Nakamura, R. Goto, Bull. Chem. Soc. Jpn. 1966, 39, 128;
39. b) H. Suzuki, Bull. Chem. Soc. Jpn. 1970, 43, 481.
40. W. Sy, B. Lodge, A. By, Synth. Commun. 1990, 20, 877.
41. K. J. Edgar, S. N. Falling, J. Org. Chem. 1990, 55, 5287.
42. H. Firouzabadi, N. Iranpoor, M. Shiri, Tetrahedron Lett. 2003, 44, 8781.
43. 2O) (20 mmol, 7.4 g) in water (100 mL) sodium hydroxide solution (15 mL) was added with stirring. Then, hydrogen peroxide solution (35%, 20 mL) was added and the resulting mixture was stirred for 15 min. The red precipitates were filtered and washed several times with distilled water and acetone, then dried in the air; yield: 4.35 g (97%).
44. a) T. Shono, Y. Matsumura, S. Katoh, K. Ikeda, T. Kamada, Tetrahedron Lett. 1989, 30, 1649;
45. b) A. Bachki, F. Foubelo, M.Yus, Tetrahedron 1994, 50, 5139;
46. c) P. Lulinski, L. Skulski, Bull. Soc. Chem. Jpn. 1997, 70, 1665;
47. d) P. Lulinski, L. Skulski, Bull. Soc. Chem. Jpn. 2000, 73, 951.