Efficient syntheses of fluorous primary phosphines that do not require PH3

Synthesis

Volumn , Issue 6, 2005, Pages 1012-1018

  Emnet, Charlotte ^a   Gladysz, J A ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Arbuzov reaction; Fluorous; Partition coefficients; Phosphines; Phosphonates

Indexed keywords

IODINE COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL); TOLUENE;

ARBUZOV REACTIONS; FLUOROPHILICITIES; FLUOROUS PHOSPHONATES; PHOSPHINES;

PHOSPHORUS COMPOUNDS;

IODIDE; LITHIUM DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TOLUENE;

ARBUZOV REACTION; ARTICLE; CHEMICAL BOND; PARTITION COEFFICIENT; SYNTHESIS;

EID: 17744383614     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-861815     Document Type: Article

References (52)

1. (a) Horváth, I. T.; Räbai, J. Science 1994, 266, 72.
2. (b) 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.
3. (c) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
4. Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004.
5. Green Reaction Media in Organic Synthesis; Mikami, K., Ed.; Blackwell: Oxford, 2005, Chap. 3, in press.
6. Da Costa, R. C.; Gladysz, J. A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 3.2.
7. (a) Schneider, S.; Tzschucke, C. C.; Bannwarth, W. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 10.8.
8. (b) Hope, E. G.; Stuart, A. M. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 10.9.
9. (c) Monflier, E.; Mortreux, A.; Castanet, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 10.10.
10. (d) Takeuchi, S.; Nakamura, Y. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 10.14.
11. Hope, E. G.; Stuart, A. M. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 10.7.
12. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138; Angew. Chem. 2004, 116, 5248; and references therein.
13. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138; Angew. Chem. 2004, 116, 5248; and references therein.
14. Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
15. For literature that has appeared since the review in ref. 6, see: (a) Hope, E. G.; Stuart, A. M.; West, A. J. Green Chem. 2004, 6, 345. (b) Vlád, G.; Richter, F.; Horváth, I. T. Org. Lett. 2004, 6, 4559.
16. For literature that has appeared since the review in ref. 6, see: (a) Hope, E. G.; Stuart, A. M.; West, A. J. Green Chem. 2004, 6, 345. (b) Vlád, G.; Richter, F.; Horváth, I. T. Org. Lett. 2004, 6, 4559.
17. (a) Alvey, L. J.; Rutherford, D.; Juliette, J. J. J.; Gladysz, J. A. J. Org. Chem. 1998, 63, 6302.
18. (b) Alvey, L. J.; Meier, R.; Soós, T.; Bernatis, P.; Gladysz, J. A. Eur. J. Inorg. Chem. 2000, 1975.
19. (a) Encyclopedia of Inorganic Chemistry, Vol. 6; King, R. B., Ed.; Wiley & Sons: New York, 1994, 3160.
20. (b) Dictionary of Inorganic Compounds, Vol. 3; Chapman & Hall: New York, 1992, 3386.
21. (c) Toy, A. D. F. In Comprehensive Inorganic Chemistry, Vol. 2; Bailar, J. C. Jr.; Emeléus, H. J.; Nyholm, R.; Trotman-Dickenson, A. F., Eds.; Pergamon: Oxford, 1973, 414.
22. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
23. (a) Fritzsche, H.; Hasserodt, U.; Korte, F. Chem. Ber. 1965, 98, 1681.
24. (b) Cabioch, J. L.; Denis, J. M. J. Organomet. Chem. 1989, 377, 227.
25. (c) Alder, R. W.; Ganter, C.; Gil, M.; Gleiter, R.; Harris, C. J.; Harris, S. E.; Lange, H.; Orpen, A. G.; Taylor, P. N. J. Chem. Soc., Perkin Trans. 1 1998, 1643.
26. (a) Jing, N.; Boardman, L. D.; Pellerite, M. J. US Patent 2,003,228,469, 2002; Chem. Abstr. 2003, 140, 5150.
27. (b) For earlier non-English-language patents that claim identical reactions, see: Enokida, T. Japanese Patent 6,032,794, 1992; Chem. Abstr. 1994, 121, 134465.
28. (c) See also: Tatsu, H.; Tachihara, K. Japanese Patent 58,180,597, 1982; Chem. Abstr. 1984, 100, 211201.
29. Other patents that describe applications of phosphonates 1 and/or 2 without reporting a synthesis: (a) Mikuni, K. Japanese Patent 9,278,969,1996; Chem. Abstr. 1997, 128, 4597. (b) Maeda, M.; Moryama, I.; Zenitani, K. Japanese Patent 8,199,034,1995; Chem. Abstr. 1996, 125, 303043.
30. Other patents that describe applications of phosphonates 1 and/or 2 without reporting a synthesis: (a) Mikuni, K. Japanese Patent 9,278,969,1996; Chem. Abstr. 1997, 128, 4597. (b) Maeda, M.; Moryama, I.; Zenitani, K. Japanese Patent 8,199,034,1995; Chem. Abstr. 1996, 125, 303043.
31. (a) Tachihara, K.; Tatsu, H. Japanese Patent 58,210,096, 1982; Chem. Abstr. 1984, 100, 210147.
32. (b) Amimoto, Y.; Shinjo, M.; Takubo, S.; Nakamae, Y. Japanese Patent 2,018,430,1988; Chem. Abstr. 1990, 113, 7893.
33. Block, H.-D. German Patent 2,514,640,1975; Chem. Abstr. 1977, 86, 72867.
34. Huang, X.-T.; Chen, Q.-Y. J. Org. Chem. 2001, 66, 4651.
35. Huang, B.-N.; Wang, K.-Y.; Huang, W.-Y.; Prescher, D. Chinese J. Chem. 1993, 11, 169.
36. Vincent, J.-M.; Rabion, A.; Yachandra, V. K.; Fish, R. H. Can. J. Chem. 2001, 79, 888.
37. Gladysz, J. A. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horvath, I. T., Eds.; Wiley/ VCH: Weinheim, 2004, Chap. 5, see Table 5-1.
38. (a) 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.
39. (b) Langer, F.; Püntener, K.; Stürmer, R.; Knöchel, P. Tetrahedron: Asymmetry 1997, 8, 715.
40. (c) Carroll, M. A.; Holmes, A. B. Chem. Commun. 1998, 1395.
41. (a) Sasse, K. Houben-Weyl, Methoden der organischen Chemie, Volume XII, Part 1; Georg Thieme Verlag: Stuttgart, 1963, 308-310.
42. (b) Voskuil, W.; Arens, J. F. Rec. Trav. Chim. Pay-Bas 1963, 82, 302.
43. (c) Shah, S.; Concolino, T.; Rheingold, A. L.; Protasiewicz, J. D. Inorg. Chem. 2000, 39, 3860.
44. Sakaki, J.-I.; Schweizer, W. B.; Seebach, D. Helv. Chim. Acta 1993, 76, 2654.
45. (a) Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189.
46. (b) Rábai, J. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 9, see Tables 9.1-6 and 9.2-6.
47. Gladysz, J. A.; Emnet, C.; Rábai, J. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley/VCH: Weinheim, 2004, Chap. 6.
48. Rocaboy, C.; Bauer, W.; Gladysz, J. A. Eur. J. Org. Chem. 2000, 2621.
49. Emnet, C.; Gladysz, J. A. manuscript in preparation.
50. Cammenga, H. K.; Epple, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1171; Angew. Chem. 1995, 107, 1284.
51. Cammenga, H. K.; Epple, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1171; Angew. Chem. 1995, 107, 1284.
52. 2.