Phase-vanishing methods based on fluorous phase screen: A simple way for efficient execution of organic synthesis

Chemical Record

Volumn 8, Issue 6, 2008, Pages 351-363

  Ilhyong, Ryu ^a   Matsubara, Hiroshi ^a   Nakamura, Hiroyuki ^b   Curran, Dennis P ^c  

^a Osaka Prefecture University   (Japan)

^b GAKUSHUIN UNIVERSITY   (Japan)

^c UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Bromination; Chlorination; Cyclopropanation; Fluorous solvent; Liquid membrane; Phase screen; Phase vanishing method; Triphasic reaction

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; FLUOROCARBON; HALOGEN; ORGANIC COMPOUND; SOLVENT;

CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS;

ALCOHOLS; ALKENES; CHEMISTRY, ORGANIC; FLUOROCARBONS; HALOGENS; ORGANIC CHEMICALS; SOLVENTS;

EID: 60849083576     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.20161     Document Type: Article

References (38)

1. For a general review of fluorous chemistry: Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds. Handbook of Fluorous Chemistry; Wiley-VCH: Weinheim, 2004.
2. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
3. Ryu, I.; Matsubara, H.; Yasuda, S.; Nakamura, H.; Curran, D. P. J Am Chem Soc 2002, 124, 12946.
4. Nakamura, H.; Usui, T.; Kuroda, H.; Ryu, I.; Matsubara, H.; Yasuda, S.; Curran, D. P. Org Lett 2003, 5, 1167.
5. Iskra, J.; Stavber, S.; Zupan, M. Chem Commun 2003, 2496.
6. Jana, N. K.; Verkade, J. G. Org Lett 2003, 5, 3787.
7. Curran, D. P.; Werner, S. Org Lett 2004, 6, 1021.
8. For the established procedures of bromination of alkenes, see: (a) Johnson, J. R.; McEwen, W. L. Org Synth Coll 1941, 1, 521;
9. (b) Snyder, H. R.; Brooks, L. A. Org Synth Coll 1943, 2, 171.
10. Pereira, S. M.; Savage, G. P.; Simpson, G. W. Syn Commun 1995, 25, 1023.
11. Yadav, J. S.; Reddy, B. V. S.; Reddy, P. S. R.; Basak, A. K.; Narsaiah, A. V. Adv Synth Catal 2004, 346, 77.
12. Rahman, Md. T.; Kamata, N.; Matsubara, H.; Ryu, I. Synlett 2005, 2664.
13. (a) Podgoršek, A.; Stavber, S.; Zupan, M.; Iskra, J. Eur J Org Chem 2006, 483;
14. (b) Iskra, J. Lett Org Chem 2006, 3, 170.
15. Matsubara, H.; Tsukida, M.; Ishihara, D.; Ryu, I. To be submitted.
16. For example: (a) Lane, C. F.; Brown, H. C. J Am Chem Soc 1970, 92, 6660;
17. (b) Lane, C. F.; Brown, H. C. J Am Chem Soc 1970, 92, 7212.
18. For example: (a) Tamao, K.; Yoshida, J.; Takahashi, M.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Kurita, A.; Kumada, M. J Am Chem Soc 1978, 100, 290;
19. (b) Hart, D. W.; Schwartz, J. J Am Chem Soc 1974, 96, 8115;
20. (c) Tolstikov, G. A.; Miftakhov, M. S.; Valeev, F. A. Izv Akad Nauk SSSR Ser Khim 1979, 2576.
21. For example: (a) Isagawa, K.; Tatsumi, K.; Otsuji, Y. Chem Lett 1977, 1117;
22. (b) Sato, F.; Sato, S.; Kodama H.; Sato, M. J Organomet Chem 1977, 142, 71;
23. (c) Gavrilenko, V. V.; Kolesov, V. S.; Zakharkin, L. I. Izv Akad Nauk SSSR, Ser Khim 1985, 681.
24. (a) McOmie, J. F. W.; Watts, M. L.; West, D. E. Tetrahedron 1968, 24, 2289;
25. (b) Benton, F. L.; Dillon, T. E. J Am Chem Soc 1942, 64, 1128.
26. For Friedel-Crafts acylation of thiophene using tin tetrachloride, see: Johnson, J. R.; May, G. E. Org Synth Coll 1943, 2, 8.
27. Matsubara, H.; Yasuda, S.; Ryu, I. Synlett 2003, 247.
28. For leading reviews of the Simmons-Smith reactions: (a) Simmons, H. E.; Cairns, T. L.; Vladuchick, S. A.; Hoiness, C. M. Org React 1973, 20, 1;
29. (b) Charette, A. B.; Beauchemin, A. Org React 2001, 58, 1.
30. 2Zn: (a) Furukawa, J.; Kawabata, N.; Nishimura, J.; Tetrahedron Lett 1966, 3353;
31. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
32. 3Al: Maruoka, K.; Fukutani, Y.; Yamamoto, H. J Org Chem 1985, 50, 4412.
33. Matsubara, H.; Tsukida, M.; Yasuda, S.; Ryu, I. J. Fluorine Chem 2008, 129, 951.
34. Nakamura, H.; Linclau, B.; Curran, D. P. J Am Chem Soc 2001, 123, 10119.
35. Luo, Z.; Swaleh, S. M.; Theil, F.; Curran, D. P. Org Lett 2002, 4, 2585.
36. Swaleh, S. M.; Hungerhofif, B.; Sonnenschein, H.; Theil, F. Tetrahedron 2002, 58, 4085.
37. 2, see: Klingenberg, J. J. Org Synth Coll 1963, 4, 110.
38. 3, see: Kirner, W. R.; Windus, W. Org Synth Coll 1943, 2, 136.