Modular synthesis of fluorous trialkylphosphines

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4559-4561

  Vlád, Gábor ^a   Richter, Frank ^b   Horváth, István T ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b Formerly Baver Material Science AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; FLUORINE DERIVATIVE; ORGANOTIN COMPOUND; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DERIVATIZATION; ORGANIC CHEMISTRY; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 10044279334     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0480675     Document Type: Article

References (22)

1. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
2. Wende, M.; Gladysz, J. A J. Am. Chem. Soc. 2003, 125, 5861.
3. Horváth, I. T. Acc. Chem. Res. 1998, 31, 341.
4. Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133.
5. (a) Parshall, G. W.; England, D. C.; Lindsey, R. V., Jr. J. Am. Chem. Soc. 1959, 81, 4801.
6. (b) Lavrent'ev, A. N.; Maslennikov, I. G.; Sochilin, E. G. Zh. Obshch. Khim. 1973, 43, 2663.
7. (c) Gopal, H.; Snyder, Jr., C. E.; Tamborski, C. J. Fluorine Chem. 1979, 14, 511.
8. (d) Nixon, J. F. Adv. Inorg. Chem. Radiochem. 1985, 29, 41.
9. (e) Alvey, L. J.; Rutherford, D.; Juliette, J. J. J.; Gladysz, J. A. J. Org. Chem. 1998, 63, 6302.
10. (f) Alvey, L. J.; Meier, R.; Soós, T.; Bernatis, P.; Gladysz, J. A. Eur. J. Inorg. Chem. 2000, 1975.
11. Kampa, J. J.; Nail, J. W.; Lagow, R. J. Angew, Chem. Int. Ed. Engl. 1995, 107, 1361.
12. Battle, S. L. Ph.D. Thesis, University of Texas, Austin, TX, 1993.
13. (a) Jiao, H.; Le Stang, S.; Soós, T.; Meier, R.; Kowski, K. Rademacher, P.; Jafarpour, L.; Hamard, J.-B.; Nolan, S. P.; Gladysz, J. A. J. Am. Chem. Soc. 2002, 124, 1516.
14. (b) Bhattacharyya, P.; Croxtall, B. Fawcett, J.; Fawcett, J.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W. Paige, D. R.; Russell, D. R.; Stuart, A. M.; Wood, D. R. W. J. Fluorine Chem. 2000, 101, 247.
15. (c) Stibrany, R.; Gorun, S. M. J. Organomet. Chem. 1999, 579, 217.
16. (a) Benefice-Malouet, S.; Blancou, H.; Commeyras, A. J. Fluorine Chem. 1985, 30, 171.
17. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P.; Tetrahedron: Assymetry 1997, 8, 715.
18. (c) Bhattacharyya, P.; Gudmunsen, D.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.; Stuart, A. M. J. Chem. Soc., Perkin Trans. 1 1997, 3609.
19. Grayson, M.; Keough, P. T.; Johnson, G. A. J. Am. Chem. Soc. 1959, 81, 4803.
20. 5f
21. 2-free FC-72. All fluorous phases were combined, and the solution was evaporated to dryness at atmospheric pressure. Drying in high vacuum at 80°C gave the corresponding fluorous phosphine. For detailed experimental data see Supporting Information.
22. The excess of the perfluoroalkyl-alkyl iodide is dissolved in dichloromethane after filtration from the phosphonium salt. After removal of the dichloromethane by rotary evaporation, the residue can be distilled to recover the pure alkylating agent, perfluoroalkyl-alkyl iodide.