η5-Rhodium(I) complexes of a λ4- phosphinine anion: Syntheses, X-ray crystal structures, and application in the catalyzed hydroformylation of olefins

Organometallics

Volumn 24, Issue 4, 2005, Pages 508-513

  Moores, Audrey ^a   Mézailles, Nicolas ^a   Ricard, Louis ^a   Floch, Pascal Le ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; CRYSTAL STRUCTURE; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SYNTHESIS (CHEMICAL); X RAYS;

CATALYTIC TRANSFORMATIONS; HYDROFORMYLATION; TURNOVER FREQUENCIES; X-RAY CRYSTALS;

RHODIUM;

EID: 14544274568     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049261y     Document Type: Article

References (63)

1. (a) Dillon, K B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: Chichester, 1998.
2. (b) Mézailles, N.; Mathey, F.; Le Floch, P. In Progress in Inorganic Chemistry; John Wiley and Sons: New York, 2001; Vol. 49, p 455.
3. Garrett, C. E.; Fu, G. C. J. Org. Chem. 1997, 62 (13), 4534-4535.
4. Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63 (13), 4168-4169.
5. (a) Sava, X.; Ricard, L.; Mathey, F.; Le Floch, P. Organometallics 2000, 19 (23), 4899-4903.
6. (b) Rosa, P.; Sava, X.; Mézailles, N.; Melaimi, M.; Ricard, L.; Mathey, F.; Le Floch, P. Phosphorus Sulfur Silicon Relat. Eiern. 2002, 177 (6-7), 1529-1532.
7. Melaimi, M.; Mathey, F.; Le Floch, P. J. Organomet Chem. 2001, 640 (1-2), 197-199.
8. Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122 (40), 9870-9871.
9. Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2001, 20 (18), 3913-3917.
10. Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125 (36), 10778-10779.
11. (a) Minami, T.; Okamoto, H.; Ikeda, S.; Tanaka, R.; Ozawa, F.; Yoshifiui, M. Angew. Chem., Int. Ed. 2001, 40 (23), 4501.
12. (b) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124 (37), 10968-10969.
13. (c) Ozawa, F.; Ishiyama, T.; Yamamoto, S.; Kawagishi, S.; Murakami, H.; Yoshifuji, M. Organometallics 2004, 23, 1698-1707.
14. (d) Liang, H. Z.; Ito, S.; Yoshifuji, M. Org. Lett. 2004, 6 (3), 425-427.
15. Daugulis, A.; Brookhart, M.; White, P. S. Organometallics 2002, 21 (26), 5935-5943.
16. Le Floch, P. In Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain; Mathey, F., Ed.; Pergamon: Palaiseau, 2001; pp 485-533.
17. (a) Mézailles, N.; Avarvari, N.; Maigrot, N.; Ricard, L.; Mathey, F.; Le Floch, P.; Cataldo, L.; Berclaz, T.; Geoffroy, M. Angew. Chem., Int. Ed. 1999, 38 (21), 3194-3197.
18. (b) Rosa, P.; Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Angew. Chem., Int. Ed. 2000, 39 (10), 1823.
19. (c) Choua, S.; Sidorenkova, H.; Berclaz, T.; Geoffroy, M.; Rosa, P.; Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. J. Am. Chem. Soc. 2000, 122 (49), 12227-12234.
20. (d) Mézailles, N.; Rosa, P.; Ricard, L.; Mathey, F.; Le Floch, P. Organometallics 2000, 19 (16), 2941-2943.
21. (e) Rosa, P.; Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P.; Jean, Y. Angew. Chem., Int. Ed. 2001, 40 (7), 1251.
22. Breit, B.; Winde, R.; Harms, K. J. Chem. Soc., Perkin Trans. 1 1997 (18), 2681-2682.
23. Breit, B.; Winde, R.; Mackewitz, T.; Paciello, R.; Harms, K. Chem.-Eur. J. 2001, 7 (14), 3106-3121.
24. Le Floch, P.; Knoch, F.; Kremer, F.; Mathey, F.; Scholz, J.; Scholz, W.; Thiele, K. H.; Zenneck, U. Eur. J. Inorg. Chem. 1998 (1), 119-126.
25. Le Floch, P.; Carmichael, D.; Mathey, F. Phosphorus Sulfur Silicon 1993, 77, 266.
26. Breit, B.; Fuchs, E. Chem. Commun. 2004, 6, 694-695.
27. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
28. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
29. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
30. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
31. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
32. For synthesis of free barrelenes, see: (a) Markl, G.; Lieb, F. Angew. Chem., Int. Ed. 1988, 7 (9), 733. (b) Ashe, A. J.; Gordon, M. D. J. Am. Chem. Soc. 1972, 94 (21), 7596. For their sulfurated version see: (c) Alcaraz, J. M.; Mathey, F. J. Chem. Soc., Chem. Commun. 1984, 8, 508-509. For their complexes, see: (d) Alcaraz, J. M.; Mathey, F. Tetrahedron Lett. 1984, 25 (2), 207-210. (e) Markl, G.; Beckh, H. J. Tetrahedron Lett. 1987, 28 (30), 3475-3478. (f) Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Eur. J. Inorg. Chem. 1999, 12, 2233-2241.
33. (a) Ashe, A. J. I.; Smith, T. W. Tetrahedron Lett. 1977, 407-410.
34. (b) Märkl, G.; Merz, A. Tetrahedron Lett. 1968, 3611-3614.
35. (c) Märkl, G.; Merz, A. Tetrahedron Lett. 1971, 1215-1218.
36. (d) Märkl, G.; Martin, C.; Weber, W. Tetrahedron Lett. 1981, 22, 1207-1210.
37. (a) Doux, M.; Bouet, C.; Mézailles, N.; Ricard, L.; Le Floch, P. Organometallicx 2002, 21 (13), 2785-2788.
38. (b) Doux, M.; Mézailles, N.; Melaimi, M.; Ricard, L.; Le Floch, P. Chem. Commun. 2002, 15, 1566-1567.
39. (c) Doux, M.; Mézailles, N.; Ricard, L.; Le Floch, P. Eur. J. Inorg. Chem. 2003, 3878-3894.
40. (d) Dochnahl, M.; Doux, M.; Faillard, E.; Ricard, L.; Le Floch, P. Eur. J. Inorg. Chem. 2004, in press.
41. Doux, M.; Mézailles, N.; Ricard, L.; Le Floch, P. Organometallics 2003, 22, 4624-4626.
42. Moores, A.; Mezailles, N.; Ricard, L.; Jean, Y.; Le Floch, P. Organometallics 2004, 23 (12), 2870-2875.
43. (a) Märkl, G.; Martin, C. Angew. Chem., Int. Ed. 1974, 13 (6), 408-409.
44. (b) Dave, T.; Berger, S.; Bilger, B.; Kaletsch, H.; Pebler, J.; Knecht, J.; Dimroth, K. Organometalliics 1966, 4 (9), 1565-1572.
45. (c) Baum, G.; Massa, W. Organometallics 1985, 4 (9), 1672-1574.
46. Moores, A.; Ricard, L.; Le Floch, P.; Mézailles, N. Organametallics 2003, 22, 1960-1966.
47. (a) Nief, F.; Fischer, J. Organometallics 1986, 5 (5), 877-883.
48. (b) Lehmkuhl, H.; Paul, R.; Kruger, C.; Tsay, Y. H.; Benn, R.; Mynott, R. Liebigs Ann. Chem. 1881, 6, 1147-1161.
49. Poyatos, M.; Uriz, P.; Mata, J. A.; Claver, C.; Fernandez, E.; Peris, E. Organometallics 2003, 22 (3), 440-444.
50. Gresham, W. F.; Brooks, R. E. (DuPont de Nemours&Co) US 2.497.303, 1950.
51. (a) Lazzaroni, R.; Raffaelli, A.; Settambolo, R.; Bertozzi, S.; Vitulli, G. 1989, 50 (1), 1-9.
52. (b) Lazzaroni, R.; Settambolo, R.; Caiazzo, A. In Rhodium Catalyzed Hydroformylation; Van Leeuwen, P., Claver, G., Eds.; Kluwer Academic Publishers: Dordrecht, 2000; pp 15-33.
53. (a) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112 (9), 3674-3676. This complex was also used as a precatalyst for hydroformylation of functionalized alkenes and alkynes.
54. (b) Alper, H.; Zhou, J. Q. J. Org. Chem. 1992, 57 (13), 3729-3731.
55. (c) Totland, K.; Alper, H. J. Org. Chem. 1993, 58 (12), 3326-3329.
56. (d) Lee, C. W.; Alper, H. J. Org. Chem. 1996, 60 (3), 499-503.
57. (e) Van den Hoven, B. G.; Alper, H. J. Org. Chem. 1990, 64 (26), 9640-9645.
58. (f) Van den Hoven, B. G.; Alper, H. J. Org. Chem. 1999, 64 (11), 3964-3968.
59. Avarvari, N.; Le Floch, P.; Mathey, F. J. Am. Chem. Soc. 1996, 118 (47), 11978-11979.
60. Doux, M.; Mézailles, N.; Ricard, L.; Le Floch, P. Eur. J. Inorg. Chem. 2003, 687.
61. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. SIR97, an integrated package of computer programs for the solution and refinement of crystal structures using single-crystal data.
62. Sheldrick, G. M. SHELXL-97; Universität Göttingen, Göttingen, Germany, 1997.
63. Farrugia, L. J. ORTEP-3; Department of Chemistry, University of Glasgow, 19XX