Nickel(II)-Promoted Homocoupling Reaction of 2-(Phosphininyl)halogenozirconocene Complexes: A New and Efficient Synthesis of 2,2′-Biphosphinines

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4826-4828

  Rosa, Patrick ^a   Mézailles, Nicolas ^a   Mathey, François ^a   Floch, Pascal Le ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000939540     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980230k     Document Type: Article

References (31)

1. For general reviews on phosphinine chemistry, see; (a) Märkl, G. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: New York, 1990; p 220. (b) Hewitt, G. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, p 639.
2. For general reviews on phosphinine chemistry, see; (a) Märkl, G. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: New York, 1990; p 220. (b) Hewitt, G. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, p 639.
3. For the use of phosphinines in homogeneous catalysis, see: (a) Knoch, F.; Kremer, U.; Zenneck, U.; Le Floch, P.; Mathey, F. Organometallics 1996, 15, 2713. (b) Böhm, D.; Geiger, H.; Knoch, F.; Kummer, S.; Le Floch, P.; Mathey, F.; Schmidt, U.; Zenneck, U. Phosphorus Sulfur 1996, 109, 173. (c) Breit, B. J. Chem. Soc., Chem. Commun. 1996, 2071. (d) Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997, 2681. (d) Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K.-H.; Zenneck, U. Eur. J. Inorg. Chem. 1998, 119.
4. For the use of phosphinines in homogeneous catalysis, see: (a) Knoch, F.; Kremer, U.; Zenneck, U.; Le Floch, P.; Mathey, F. Organometallics 1996, 15, 2713. (b) Böhm, D.; Geiger, H.; Knoch, F.; Kummer, S.; Le Floch, P.; Mathey, F.; Schmidt, U.; Zenneck, U. Phosphorus Sulfur 1996, 109, 173. (c) Breit, B. J. Chem. Soc., Chem. Commun. 1996, 2071. (d) Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997, 2681. (d) Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K.-H.; Zenneck, U. Eur. J. Inorg. Chem. 1998, 119.
5. For the use of phosphinines in homogeneous catalysis, see: (a) Knoch, F.; Kremer, U.; Zenneck, U.; Le Floch, P.; Mathey, F. Organometallics 1996, 15, 2713. (b) Böhm, D.; Geiger, H.; Knoch, F.; Kummer, S.; Le Floch, P.; Mathey, F.; Schmidt, U.; Zenneck, U. Phosphorus Sulfur 1996, 109, 173. (c) Breit, B. J. Chem. Soc., Chem. Commun. 1996, 2071. (d) Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997, 2681. (d) Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K.-H.; Zenneck, U. Eur. J. Inorg. Chem. 1998, 119.
6. For the use of phosphinines in homogeneous catalysis, see: (a) Knoch, F.; Kremer, U.; Zenneck, U.; Le Floch, P.; Mathey, F. Organometallics 1996, 15, 2713. (b) Böhm, D.; Geiger, H.; Knoch, F.; Kummer, S.; Le Floch, P.; Mathey, F.; Schmidt, U.; Zenneck, U. Phosphorus Sulfur 1996, 109, 173. (c) Breit, B. J. Chem. Soc., Chem. Commun. 1996, 2071. (d) Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997, 2681. (d) Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K.-H.; Zenneck, U. Eur. J. Inorg. Chem. 1998, 119.
7. For the use of phosphinines in homogeneous catalysis, see: (a) Knoch, F.; Kremer, U.; Zenneck, U.; Le Floch, P.; Mathey, F. Organometallics 1996, 15, 2713. (b) Böhm, D.; Geiger, H.; Knoch, F.; Kummer, S.; Le Floch, P.; Mathey, F.; Schmidt, U.; Zenneck, U. Phosphorus Sulfur 1996, 109, 173. (c) Breit, B. J. Chem. Soc., Chem. Commun. 1996, 2071. (d) Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997, 2681. (d) Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K.-H.; Zenneck, U. Eur. J. Inorg. Chem. 1998, 119.
8. Mathey, F.; Le Floch, P. Chem. Ber. 1996, 129, 263.
9. (a) van der Sluis, M.; Wit, J. B. M.; Bickelhaupt, F. Organometallics 1996, 15, 174.
10. (b) van der Sluis, M.; Beverwijk, V.; Termaten, A.; Gavrilova, E.; Bickelhaupt, F.; Kooijman, H.; Veldman, N.; Spek, A. L. Organometallics 1997, 16, 1144.
11. (c) Cénac, N.; Chrostowska, A.; Sotiropoulos, J.-M.; Donnadieu, B.; Igau, A.; Pfister-Guillouzo, G.; Majoral, J. P. Organometallics 1997, 16, 4551.
12. (a) Märkl, G.; Lieb, F.; Merz, A. Angew. Chem., Int. Ed. Engl. 1967, 6, 87.
13. (b) Märkl, G.; Merz, A. Tetrahedron Lett. 1971, 17, 1215.
14. (c) Ashe, A. J., III; Smith, T. W. Tetrahedron Lett. 1977, 5, 407.
15. (a) Le Floch, P.; Carmichael, D.; Ricard, L.; Mathey, F. J. Am. Chem. Soc. 1991, 113, 667.
16. (b) Holand, S.; Ricard, L.; Mathey, F. J. Org. Chem. 1991, 56, 4031.
17. (c) Trauner, H.; Le Floch, P.; Lefour, J. M.; Ricard, L.; Mathey, F. Synthesis 1995, 6, 717.
18. (d) Le Floch, P.; Ricard, L.; Mathey, F. Bull. Soc. Chim. Fr. 1994, 131, 330.
19. Le Floch, P.; Carmichael, D.; Ricard, L.; Mathey, F.; Jutand, A.; Amatore, C. Organometallics 1992, 11, 2475.
20. (a) Teunissen, H. T.; Bickelhaupt, F. Tetrahedron Lett. 1992, 33, 3537.
21. (b) Teunissen, H. T.; Bickelhaupt, F. Bull. Soc. Chim. Belg, 1992, 101, 609.
22. (c) Teunissen, H. T.; Bickelhaupt, F. Organometallics 1996, 15, 794.
23. (d) Teunissen, H. T.; Bickelhaupt, F. Organometallics 1996, 15, 802.
24. Le Floch, P.; Ricard, L.; Mathey, F. J. Chem. Soc., Chem. Commun. 1993, 789.
25. Negishi, E.; Holmes, S. J.; Tour, J. H.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. S.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
26. Sacconi, L.; Mani, F.; Bencini, A. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: New York, 1987; Vol. 5, p 1.
27. (a) Negishi, E.; Van Horn, D. E. J. Am. Chem. Soc. 1977, 99, 3168.
28. (b) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
29. (a) Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333.
30. (b) Dayrit, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466.
31. Booth, J.; Chatt, J. J. Chem. Soc. 1965, 3238.