Regioselective zirconophosphination of 1-alkenes: A versatile route for the synthesis of β-functionalized alkyldiphenylphosphine oxides in the presence of CuCl

Organometallics

Volumn 27, Issue 15, 2008, Pages 3834-3839

  Xi, Chanjuan ^a,b   Yan, Xiaoyu ^a,b   Lai, Chunbo ^a,b   Kanno, Ken Ichiro ^c   Takahashi, Tamotsu ^c  

^a Tsinghua University   (China)

^b NANKAI UNIVERSITY   (China)

^c HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; COPPER COMPOUNDS; HYDROCARBONS; ZIRCONIUM COMPOUNDS;

1-ALKENES; FUNCTIONALIZED; REGIO-SELECTIVE; SYNTHESIS OF; ZIRCONOCENE;

COMPLEXATION;

EID: 50549096080     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om701253d     Document Type: Article

References (67)

1. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
2. (b) Omac, J. Application of Organometallic Compounds; Wiley: Toronto, 1999.
3. (c) Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. N., Jordon, F., Stone, A., Wilkinson, J., Eds.; Pergamon Press: New York, 1995; Vols. 9 and 12.
4. (d) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1999.
5. (a) Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996.
6. (b) Homogeneous Catalysis with Metal-Phosphine Complexes; Pignolet, L. H., Ed.; Plenum Press: New York, 1983.
7. (a) Han, L.-B.; Mizaeri, F.; Zhao, Ch.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407.
8. (b) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
9. (c) Keller, J.; Schlierf, C.; Nolte, C.; Mayer, P.; Straub, B. F. Synthesis 2006, 354.
10. For example, see:(a) The Chemistry of Functional Groups - The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1990-1992.
11. (b) Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Decker: New York, 1992.
12. (a) Wolfsberger, W. Chem. Zeitung 1988, 112, 53.
13. (b) Delacroix, O.; Gaumont, A. C. Curr. Org. Chem. 2005, 9, 1851.
14. 3 to a double bond is limited to Michael-type activated alkenes:(a) Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223.
15. (b) Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701.
16. (c) Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht,: The Netherlands, 1995; Vol. 5, p 111.
17. (d) Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277.
18. (e) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039.
19. (f) Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49.
20. (g) Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255.
21. (h) Wicht, D. K.; Kourkine, I. V.; Kovacik, I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381.
22. (i) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141.
23. (j) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950.
24. (k) Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824.
25. (l) Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357.
26. (m) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
27. (a) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880.
28. (b) Douglas, T.; Theopold, K. H. Angew. Chem., Int. Ed. Engl. 1989, 28, 1367.
29. (c) Doherty, S.; Eastham, G. R.; Tooze, R. P.; Scanhan, T. H.; Williams, D.; Elsegood, R. M. R. J.; Clegg, W. Organometallics 1999, 18, 3558.
30. (d) Hay, C.; Vilain, D. L.; Deborde, V.; Toupet, L.; Réau, R. Chem. Commun. 1999, 345.
31. (e) Hydrio, J.; Gouygou, M.; Dallemer, F.; Daran, J. C.; Balavoine, G. G. A. J. Organomet. Chem. 2000, 595, 261.
32. (f) Doherty, S.; Knight, J. G.; Robins, E. G.; Scanlan, T. H.; Champkin, P. A.; Clegg, W. J. Am. Chem. Soc. 2001, 123, 5110.
33. (g) Doherty, S.; Robins, E. G.; Nieuwenhuyzen, M.; Knight, J. G.; Champ, P. A. Organometallics 2002, 21, 1383.
34. (h) Miyaji, T.; Xi, Z.; Nakajima, K.; Takahashi, T. Organometallics 2001, 20, 2859.
35. (i) Nishihara, Y.; Aoyagi, K.; Hara, R.; Suzuki, N.; Takahashi, T. Inorg. Chim. Acta 1996, 91.
36. (j) Mao, S. S. H.; Don Tilley, T. Macromolecules 1997, 30, 5566.
37. (a) Miquel, Y.; Igau, A.; Donnadieu, B.; Majoral, J. P.; Dupuis, L.; Pirio, N.; Meunier, P. Chem. Commun. 1997, 279.
38. (b) Zablocka, M.; Igau, A.; Majorai, J.-P.; Pietrueiewicz, K. M. Organometallics 1993, 12, 603.
39. (c) Cadierno, V.; Zablocka, M.; Donnadieu, M.; Lgau, A.; Majoral, J. P. New J. Chem. 2003, 27, 675.
40. Xi, Z.; Zhang, W.; Takahashi, T. Tetrahedron Lett. 2004, 45, 2427.
41. (a) Xi, C.; Ma, M.; Li, X. Chem. Commun. 2001, 2554.
42. (b) Lai, C.; Xi, C.; Chen, C.; Ma, M.; Hong, X. Chem. Commun. 2003, 2736.
43. (c) Lai, C.; Xi, C.; Chen, W.; Hua, R. Tetrahedron 2006, 62, 6295.
44. Xi, C.; Yan, X.; Lai, C. Organometallics 2007, 26, 1084.
45. (a) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1989, 27, 2829.
46. (b) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623.
47. Swanson, D. R.; Negishi, E. Organometallics 1991, 10, 825.
48. (a) Kuchen, W.; Buchwald, H. Chem. Ber 1958, 91, 2871.
49. (b) Spanier, E. J.; Caropreso, F. E. J. Am. Chem. Soc. 1970, 92, 3348.
50. (c) Cowley, A. H. Chem. Rev. 1965, 65, 617.
51. (a) Wagenen, B. C. V.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495.
52. (b) Negishi, E.; Swanson, D. R.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
53. (a) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N.; Nakajima, N. Organometallics 1994, 13, 4183.
54. (b) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154.
55. (c) Xi, C.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2000, 65, 945.
56. (a) Erker, G.; Dorf, U.; Mynott, R.; Tsay, Y.-H.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1985, 24, 584.
57. (b) Buchwald, S. L.; Watson, B. T. J. Am. Chem. Soc. 1987, 109, 2544.
58. (c) Takahashi, T.; Suzuki, N.; Kaheyama, M.; Kondakov, D. Y.; Hara, R. Tetrahedron Lett. 1993, 34, 4811.
59. (a) Hey-Hawkins, E.; Lindenberg, F. Chem. Ber. 1992, 125, 1815.
60. (b) Matthias, W.; Matthias, H. D.; Heinrich, N.; Thomas, S.; Arno, P. J. Am. Chem. Soc. 1998, 120, 6722.
61. Gordillo, B.; Dominguez, Z. J.; Sanchez, N.; Gonzalez, R.; Salas, M.; Barragan, E. Tetrahedron Lett. 2003, 44, 5293.
62. (a) Nelson, A.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1997, 2645.
63. (b) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411.
64. Renard, P.-Y.; Vayron, P.; Mioskowski, C. Org. Lett. 2003, 5, 1661.
65. Bartels, B.; Clayden, J.; Martin, C. G.; Nelson, A.; Russell, M. G.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1999, 1807.
66. Takaki, K.; Koshoji, G.; Komeyama, K.; Takeda, M.; Shishido, T.; Kitani, A.; Takehira, K. J. Org. Chem. 2003, 68, 6554.
67. Carta, P.; Puljic, N.; Robert, C.; Dhimane, A.-L.; Fensterbank, L.; Lacote, E.; Malacria, M. Org. Lett. 2007, 9, 1061.