Fluorous solvent as a new phase-screen medium between reagents and reactants in the bromination and chlorination of alcohols

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1167-1169

  Nakamura, Hiroyuki ^a   Usui, Taikou ^a   Kuroda, Hirokazu ^a   Ryu, Ilhyong ^b   Matsubara, Hiroshi ^b   Yasuda, Shinji ^b   Curran, Dennis P ^c  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CHLORIDE; CHLORINE DERIVATIVE; FLUORINE DERIVATIVE; PERFLUORO COMPOUND; SOLVENT;

ARTICLE; BROMINATION; CHLORINATION; REGULATORY MECHANISM; SCREENING; TECHNIQUE;

EID: 0141629302     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034060w     Document Type: Article

References (32)

1. (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
2. (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
3. (a) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
4. (b) Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2057.
5. (c) Kitazume, T. J. Fluorine Chem. 2000, 105, 265.
6. (d) Furin, G. G. Russ. Chem. Rev. 2000, 69, 491.
7. (a) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183.
8. (b) Fish, R. H. Chem. Eur. J. 1999, 5, 1677.
9. (c) de Wolf, E.; van Koten, G.; Deelman, B. J. Chem. Soc. Rev. 1999, 28, 37.
10. (d) Dinh, L. V.; Gladysz, J. Tetrahedron Lett. 1999, 40, 8995.
11. (e) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 2000, 41, 57.
12. (f) Alvey, L. J.; Meier, R.; Soos, T.; Bernatis, P.; Gladysz, J. A. Eur. J. Org. Chem. 2000, 1975.
13. (g) Rocaboy, C.; Bauer, W.; Gladysz, J. A. Eur. J. Org. Chem. 2000, 2621.
14. (h) Barrett, A. N.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847.
15. (a) Curran, D. P. J. Am. Chem. Soc. 1996, 118, 2531.
16. (b) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
17. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
18. (d) Hadida, S.; Super, M. S.; Beckman, E. J.; Curran, D. P. J. Am. Chem. Soc. 1997, 119, 7406.
19. (e) Curran, D. P.; Hadida, S.; Kim, S.-Y.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 6607.
20. (f) Linclau, B.; Sing, A. K.; Curran, D. P. J. Org. Chem. 1999, 64, 2835.
21. (g) Curran, D. P.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 9069.
22. (h) Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766.
23. (a) Ryu, I.; Matsubara, H.; Yasuda, S.; Nakamura, H.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 12946.
24. (b) Matsubara, H.; Yasuda, S.; Ryu, I. Synlett 2003, 247.
25. (a) Nakamura, H.; Linclau, B.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 10119.
26. (b) Luo, Z.; Swaleh, S. M.; Theil, F.; Curran, D. P. J. Org. Chem. 2002, 4, 2582.
27. 3, see: (a) Organic Syntheses; Gilman, H., Ed.; Wiley: New York, 1941; Collect. Vol. I, p 36. (b) Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York, 1943; Collect. Vol. II, p 358.
28. 3, see: (a) Organic Syntheses; Gilman, H., Ed.; Wiley: New York, 1941; Collect. Vol. I, p 36. (b) Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York, 1943; Collect. Vol. II, p 358.
29. 3, see: (a) Organic Syntheses; Rabjohn, N., Ed.; Wiley: New York, 1963; Collect. Vol. IV, p 110. (b) Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York, 1943; Collect. Vol. II, p 136.
30. 3, see: (a) Organic Syntheses; Rabjohn, N., Ed.; Wiley: New York, 1963; Collect. Vol. IV, p 110. (b) Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York, 1943; Collect. Vol. II, p 136.
31. Chaudhari, S. S.; Akamanchi, K. G. Synlett 1999, 1763.
32. 2 layer vanished after 3-5 h. The reaction progress was monitored by GC or TLC analysis. After the reaction was completed (between 4 h and 3 days), the toluene layer was decanted and poured into water. The mixture was extracted with ether, washed with a saturated NaCl aqueous solution, and concentrated. The residue was purified by column chromatography on silica gel with hexane (or ether) to give 3.