Synthesis, structures, and reactions of dirhodium complexes bearing a 1,2-Diphenyl-3,4-diphosphinidenecyclobutene ligand (DPCB)

Organometallics

Volumn 28, Issue 3, 2009, Pages 902-908

  Okazaki, Masaaki ^a   Hayashi, Akito ^a   Fu, Ching Feng ^b   Liu, Shiuh Tzung ^b   Ozawa, Fumiyuki ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BEARINGS (STRUCTURAL); CARBON MONOXIDE; CHELATION; ELECTRONIC PROPERTIES; LIGANDS; PHOSPHORUS; RHODIUM;

CO ATMOSPHERES; CYCLOBUTENE; CYCLOHEXADIENE; DIRHODIUM COMPLEXES; HYDRIDO COMPLEXES; PHOSPHINIDENE; PHOSPHORUS LIGANDS; PLANAR CONFIGURATIONS; STABLE FORMS; TETRAHEDRAL ARRANGEMENTS; X-RAY STRUCTURES;

RHODIUM COMPOUNDS;

EID: 61849090930     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8010799     Document Type: Article

References (81)

1. (a) Le Floch, P. Coord. Chem. Rev. 2006, 250, 627.
2. (b) Yoshifuji, M. Pure Appl. Chem. 2005, 77, 2011.
3. (c) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578.
4. (d) Weber, L. Angew. Chem., Int. Ed. 2002, 41, 563.
5. (a) Deschamps, B.; Le Goff, X.; Ricard, L.; Le Floch, P. Heteroat. Chem. 2007, 18, 363.
6. (b) Masuda, J. D.; Martin, D.; Lyon-Saunier, C; Baceiredo, A.; Gornitzka, H.; Donnadieu, B.; Bertrand, G. Chem. Asian J. 2007, 2, 178.
7. (c) Ionkin, A. S.; Marshall, W. J.; Fish, B. M.; Schiffhauer, M. F.; Davidson, F.; McEwen, C. N.; Keys, D. E. Organometallics 2007, 26, 5050.
8. (d) Nakamura, A.; Kawasaki, S.; Toyota, K.; Yoshifuji, M. J. Organomet. Chem. 2007, 692, 70.
9. (e) Mézailles, N.; Le Floch, P. Dalton Trans. 2006, 594.
10. (f) Ito, S.; Freytag, M.; Yoshifuji, M. Dalton Trans. 2006, 710.
11. (g) Freytag, M.; Ito, S.; Yoshifuji, M. Chem. Asian J. 2006, 1, 693.
12. (h) Ito, S.; Nishide, K.; Yoshifuji, M. Organometallics 2006, 25, 1424.
13. (i) Gouverd, C; Brynda, M.; Berclaz, T.; Geoffroy, M. J. Organomet. Chem. 2006, 691, 72.
14. (j) Kawasaki, S.; Nakamura, A.; Toyota, K.; Yoshifuji, M. Organometallics 2005, 24, 2983.
15. (k) Boubekeur, L.; Ricard, L.; Le Floch, P.; Mézailles, N. Organometallics 2005, 24, 3856.
16. (l) Nishide, K.; Liang, H.; Ito, S.; Yoshifuji, M. J. Organomet. Chem. 2005, 690, 4809.
17. (m) Martin, D.; Baceiredo, A.; Gornitzka, H.; Schoeller, W. W.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 1700.
18. (n) Nakamura, A.; Kawasaki, S.; Toyota, K.; Yoshifuji, M. Chem. Lett. 2004, 33, 1570.
19. (o) Liang, H.; Ito, S.; Yoshifuji, M. Org. Lett. 2004, 6, 425.
20. (p) Ionkin, A.; Marshall, W. Chem. Commun. 2003, 710.
21. (q) Moores, A.; Mézailles, N.; Ricard, L.; Mathey, F.; Le Floch, P. Chem. Commun. 2003, 1914.
22. (r) Spencer, L. P.; Altwer, R.; Wei, P.; Gelmini, L.; Gauld, J.; Stephan, D. W. Organometallics 2003, 22, 3841.
23. (s) Daugulis, A.; Brookhart, M.; White, P. S. Organometallics 2002, 21, 5935.
24. Ozawa, F.; Kawagishi, S.; Ishiyama, T.; Yoshifuji, M. Organometallics 2004, 23, 1325.
25. (a) Ozawa, F.; Yoshifuji, M. Dalton Trans. 2006, 4987.
26. (b) Ozawa, F.; Yoshifuji, M. C. R. Chim. 2004, 7, 747.
27. (a) Hayashi, A.; Yoshitomi, T.; Umeda, K.; Okazaki, M.; Ozawa, F. Organometallics 2008, 27, 2321.
28. (b) Jensen, R. S.; Umeda, K.; Okazaki, M.; Ozawa, F.; Yoshifuji, M. J. Organomet. Chem. 2007, 692, 286.
29. (c) Murakami, H.; Matsui, Y.; Ozawa, F.; Yoshifuji, M. J. Organomet. Chem. 2006, 691, 3151.
30. (d) Katayama, H.; Nagao, M.; Nishimura, T.; Matsui, Y.; Umeda, K.; Akamatsu, K.; Tsuruoka, T.; Nawafune, H.; Ozawa, F. J. Am. Chem. Soc. 2005, 127, 4350.
31. (e) Nagao, M.; Asano, K.; Umeda, K.; Katayama, H.; Ozawa, F. J. Org. Chem. 2005, 70, 10511.
32. (f) Gajare, A. S.; Jensen, R. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Synlett 2005, 144.
33. (g) Jensen, R. S.; Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Tetrahedron Lett. 2005, 46, 8645.
34. (h) Ozawa, F.; Ishiyama, T.; Yamamoto, S.; Kawagishi, S.; Murakami, H.; Yoshifuji, M. Organometallics 2004, 23, 1698.
35. (i) Murakami, H.; Minami, T.; Ozawa, F. J. Org. Chem. 2004, 69, 4482.
36. (j) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. J. Org. Chem. 2004, 69, 6504.
37. (k) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 1994.
38. (l) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
39. (m) Minami, T.; Okamoto, H.; Ikeda, S.; Tanaka, R.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2001, 40, 4501.
40. (n) Ozawa, F.; Yamamoto, S.; Kawagishi, S.; Hiraoka, M.; Ikeda, S.; Minami, T.; Ito, S.; Yoshifuji, M. Chem. Lett. 2001, 972.
41. (o) Ikeda, S.; Ohhata, F.; Miyoshi, M.; Tanaka, R.; Minami, T.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2000, 39, 4512.
42. (a) Giije, J. W.; Roesky, H. W. Chem. Rev. 1994, 94, 895.
43. (b) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
44. Fandos, R.; Hernández, C; Otero, A.; Rodríguez, A.; Ruiz, M. J. Organometallics 1999, 18, 2718, and references therein.
45. (a) Mizuno, T.; Alper, H. J. Mol. Catal. A 1997, 121, 119.
46. (b) Mizuno, T.; Alper, H. J. Mol. Catal. A 1997, 123, 21.
47. (c) Grushin, V. V.; Kuznetsov, V. F.; Bensimon, C; Alper, H. Organometallics 1995, 14, 3927.
48. (d) Brune, H.-A.; Unsin, J.; Hemmer, R.; Reichhardt, M. J. Organomet. Chem. 1989, 369, 335.
49. (e) Brune, H.-A.; Hemmer, R.; Unsin, J.; Holl, K.; Thewalt, U. Z Naturforsh., B 1988, 43, 487.
50. (a) Nishimura, T.; Katoh, T.; Hayashi, T. Angew. Chem., Int. Ed. 2007, 46, 4937.
51. (b) Nishimura, T.; Hirabayashi, S.; Yasuhara, Y.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 2556.
52. (c) Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 3904.
53. (d) Kina, A.; Yasuhara, Y.; Nishimura, T.; Iwamura, H.; Hayashi, T. Chem. Asian J. 2006, 1, 707.
54. (e) Miura, T.; Shimada, M.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1094.
55. (f) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872.
56. (g) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
57. (h) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
58. (i) Hayashi, T.; Tokunaga, N.; Yoshida, K.; Han, J. W. J. Am. Chem. Soc. 2002, 124, 12102.
59. (a) Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876.
60. (b) Krug, C; Hartwig, J. F. Organometallics 2004, 23, 4594.
61. (a) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806.
62. (b) Herrmann, W. A.; Kulpe, J. A.; Konkol, W.; Bahrmann, H. J. Organomet. Chem. 1990, 389, 85.
63. (a) Johansson, R.; Wendt, O. F. Organometattics 2007, 26, 2426.
64. (b) Torresan, I.; Michelin, R. A.; Marsella, A.; Zanardo, A.; Pinna, F.; Strukul, G. Organometallics 1991, 10, 623.
65. (c) Bennett, M. A. J. Mol. Catal. 1987, 41, 1.
66. A similar coordination mode of DPCB has been reported for a tungsten complex: Yoshifuji, M.; Ichikawa, Y.; Yamada, N.; Toyota, K. Chem. Commun. 1998, 27.
67. 2core deserve discussion.
68. (a) The sum of the four angles around Rhl: 360.2°.
69. (b) The sum of the four angles around Rh2: 405.2°.
70. (a) Cotton, F. A. Prog. Inorg. Chem. 1976, 21, 1.
71. (b) Colton, R.; McCormick, M. J. Coord. Chem. Rev. 1980, 31, 1.
72. For examples of di-μ-carbonyl-dirhodium complexes, see: (a) Singh, P.; Dammann, C. B.; Hodgson, D. J. Inorg. Chem. 1973, 12, 1335.
73. (b) Burch, R. R.; Muetterties, E. L.; Schultz, A. J.; Gebert, E. G.; Williams, J. M. J. Am. Chem. Soc. 1981, 103, 5517.
74. (c) James, B. R.; Mahajan, D.; Rettig, S. J.; Williams, G. M. Organometallics 1983, 2, 1452.
75. (d) Freeman, M. A.; Young, D. A. Inorg. Chgem. 1986, 25, 1556.
76. (e) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L. Organometallics 1987, 6, 101.
77. (f) Cecconi, F.; Chilardi, C. A.; Midollini, S.; Orlandini, A.; Zanello, P.; Heaton, B. T.; Huang, L.; Iggo, J. A.; Bordoni, S. J. Organomet. Chem. 1988, 353, C5.
78. (g) Douglas, S.; Lowe, J. P.; Mahon, M. F.; Warren, J. E.; Whittlesey, M. K. J. Organomet. Chem. 2005, 690, 5027.
79. 2 were carried out with the Gaussian 98 program (Revision A.9, Gaussian, Inc., 1998) using B3LYP in conjunction with the standard LanL2DZ basis set and effective core potentials for Rh and 6-31G(d) basis set for other atoms. This examination showed the Mulliken atomic charges of Rhl (-0.14) and Rh2 (+0.38).
80. Cramer, R. Inorg. Synth. 1974, 15, 14.
81. Sheldrick, G. M. SHELX-97; University of Göttingen: Germany, 1997.