Conversion of alcohols to bromides using a fluorous phosphine

Tetrahedron Letters

Volumn 44, Issue 41, 2003, Pages 7589-7591

  Desmaris, Laurence ^a   Percina, Nathalie ^a   Cottier, Louis ^a   Sinou, Denis ^a  

^a CPE LYON   (France)

Author keywords

Fluorous solvent; Fluorous triphenylphosphine; Recycling; Tetrabromomethane

Indexed keywords

ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; CARBON TETRACHLORIDE; PHOSPHINE DERIVATIVE; POLYMER; TOLUENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; GAS CHROMATOGRAPHY; LIQUID LIQUID EXTRACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141629390     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.064     Document Type: Article

References (31)

1. Larock R.C. Comprehensive Organic Transformations. 1989;353-360 VCH, New York.
2. Appel R. Angew. Chem., Int. Ed. Engl. 14:1975;801.
3. Harrison C.R., Hodge P., Hunt B.J., Khoshdel E., Richardson G. J. Org. Chem. 48:1983;3721-3728.
4. Arstad E., Barrett A.G.M., Hopkins B.T., Köbberling J. Org. Lett. 4:2002;1975-1977.
5. Caldarelli M., Habermann J., Ley S.V. J. Chem. Soc., Perkin Trans. 1. 1999;107-110.
6. Pollastri M.P., Sagal J.F., Chang G. Tetrahedron Lett. 42:2001;2459-2460.
7. Horvath I.T., Rabai J. Science. 266:1994;72-75.
8. Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2532.
9. Horner J.H., Martinez F.N., Newcombe M., Hadida S., Curran D.P. Tetrahedron Lett. 38:1997;2783-2786.
10. Curran D.P., Hadida S., Kim S.-Y., Luo Z. J. Am. Chem. Soc. 121:1999;6607-6615.
11. Ryu I., Curran D.P. Tetrahedron Lett. 40:1999;2367-2370.
12. Crich D., Hao X., Lucas M. Tetrahedron. 55:1999;14261-14268.
13. Crich D., Hao X., Lucas M.A. Org. Lett. 1:1999;269-271.
14. Bhattacharyya P., Gudmunsen D., Hope E.G., Kemmit R.D.W., Paige D.R., Stuart A.M. J. Chem. Soc., Perkin Trans. 1. 1997;609-3612.
15. Chen W., Xiao J. Tetrahedron Lett. 41:2000;3697-3700.
16. Galante A., Lhoste P., Sinou D. Tetrahedron Lett. 42:2001;5424-5427.
17. Barthelemy S., Scheider S., Bannwarth W. Tetrahedron Lett. 43:2002;807-810.
18. Lindsley C.W., Zhou Z., Newton R.C., Leister W.H., Strauss K.A. Tetrahedron Lett. 43:2002;4467-4470.
19. Dobbs A.P., McGregor-Johnson C. Tetrahedron Lett. 43:2002;2807-2810.
20. Dandapani J.C., Curran D.P. Tetrahedron. 58:2002;3855-3864.
21. Curran D.P., Ferritto R., Hua Y. Tetrahedron Lett. 39:1998;4937-4940.
22. Wipf P., Reeves J.T. Tetrahedron Lett. 40:1999;4649-4652.
23. Wipf P., Reeves J.T. Tetrahedron Lett. 40:1999;5139-5142.
24. Röver S., Wipf P. Tetrahedron Lett. 40:1999;5667-5670.
25. Pardo J., Cobas A., Guitian E., Castedo L. Org. Lett. 3:2001;3711-3714.
26. Luo Z., Williams J., Williams R.W., Read R.W., Curran D.P. J. Org. Chem. 66:2001;4261-4266.
27. Miura T., Inazu T. Tetrahedron Lett. 44:2003;119-122.
28. Mizuno M., Goto K., Miura T., Hosaka D., Inazu T. Chem. Commun. 2003;972-973.
29. Maillard D., Pozzi G., Sinou D. Eur. J. Org. Chem. 2002;269-275.
30. 4 (94 mg, 0.28 mmol). To this solution was added the alcohol (0. 28 mmol), and the mixture was stirred at 50°C for the desired time. The solution was cooled to rt, and the fluorous-phosphine oxide was extracted with FC-72 (4×2 mL). Evaporation of the hydrocarbon phase gave the bromide, and evaporation of the fluorous phase gave the fluorous-phosphine oxide.
31. Wagner A., Heitz M.P., Mioskowski C. Tetrahedron Lett. 30:1989;557-558.