Sandwich complexes containing bent palladium chains

Angewandte Chemie - International Edition

Volumn 45, Issue 35, 2006, Pages 5799-5803

  Tatsumi, Yasuki ^a   Shirato, Katsunori ^a   Murahashi, Tetsuro ^a,b   Ogoshi, Sensuke ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Chain structures; Palladium; pi interactions; Sandwich complexes; Structure elucidation

Indexed keywords

GEOMETRY; MOLECULAR STRUCTURE; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

CHAIN STRUCTURES; PI INTERACTIONS; SANDWICH COMPLEXES; STRUCTURE ELUCIDATION;

PALLADIUM COMPOUNDS;

EID: 33748568831     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601641     Document Type: Article

References (47)

1. a) T. J. Kealy, P. L. Pauson, Nature 1951, 168, 1039;
2. b) S. A. Miller, J. A. Tebboth, J. F. Tremaine, J. Chem. Soc. 1952, 632;
3. c) G. Wilkinson, M. Rosenblum, M. C. Whiting, R. B. Woodward, J. Am. Chem. Soc. 1952, 74, 2125;
4. d) E. O. Fischer, W. Z. Pfab, Z. Naturforsch. B 1952, 7, 377.
5. a) Metallocenes: Synthesis-Reactivity-Applications (Eds.: A. Togni, R. L. Halterman), Wiley-VCH, New York, 2000;
6. b) N. J. Long, Metallocenes, Blackwell Science, Oxford, 1998.
7. a) T. Murahashi, E. Mochizuki, Y. Kai, H. Kurosawa, J. Am. Chem. Soc. 1999, 121, 10 660;
8. b) T. Murahashi, T Nagai, T. Okuno, T. Matsutani, H. Kurosawa, Chem. Commun. 2000, 1689;
9. c) T. Murahashi, T. Nagai, Y. Mino, E. Mochizuki, Y. Kai, H. Kurosawa, J. Am. Chem. Soc. 2001, 123, 6927;
10. d) T. Murahashi, Y. Higuchi, T. Katoh, H. Kurosawa, J. Am. Chem. Soc. 2002, 124, 14 288;
11. e) Y. Tatsumi, T. Nagai, H. Nakashima, T. Murahashi, H. Kurosawa, Chem. Commun. 2004, 1430;
12. f) T. Murahashi, H. Nakashima, T. Nagai, Y. Mino, T. Okuno, M. A. Jalil, H. Kurosawa, J. Am. Chem. Soc. 2006, 128, 4377.
13. A review on metal-metal chain compounds: J. K. Bera, K. R. Dunbar, Angew. Chem. 2002, 114, 4633;
14. Angew. Chem. Int. Ed. 2002, 41, 4453.
15. 2+ (dpdp = all-trans,s-trans-1,10-diphenyl-1,3,5,7,9- decapentaene) and 1, respectively. T. Murahashi, H. Kurosawa et al., unpublished results.
16. T. Murahashi, T. Uemura, H. Kurosawa, J. Am. Chem. Soc. 2003, 125, 8436.
17. o-BPBB was prepared by the Wittig reaction; the experimental details are given in the Supporting Information,
18. R. N. McDonald, T. W. Champbell, J. Org. Chem. 1959, 24, 1969.
19. -1, T = 133 K, 835 variables refined with 24 034 reflections with I > 3σ(I) to R1 = 0.091. CCDC-604663 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
20. T. Murahashi, H. Kurosawa, Coord. Chem. Rev. 2002, 231, 207.
21. 4)(CH=CH)Ph range from 1.378 to 1.412 Å: A. Böhm, M. Adam, H. Mauermann, S. Stein, K. Müllen, Tetrahedron Lett. 1992, 33, 2795.
22. o-Xylylene is known to form stable complexes with transition metals. For several examples of π-bonded o-xylylene complexes, see: a) W. R. Roth, J. D. Meier, Tetrahedron Lett. 1967, 8, 2053;
23. b) R. Victor, R. Ben-Shoshan, J. Organomet. Chem. 1974, 80, C1;
24. c) S. D. Chappell, D. J. Cole-Hamilton, J. Chem. Soc. Chem. Commun. 1981, 319;
25. d) J. W. Hull Jr., W. L. Gladfelter, Organometallics 1982, 1, 1716;
26. e) A. M. Madonilc, D. Asruc, J. Am. Chem. Soc. 1984, 106, 2437;
27. f) J. M. Grosselin, H. L. Bozec, C. Moinet, L. Toupet, P. H. Dixneuf, J. Am. Chem. Soc. 1985, 107, 2809;
28. g) J.-M. Grosselin, H. L. Bozec, C. Moinet, L. Toupet, F. H. Köhler, P. H. Dixneuf, Organometallics 1988, 7, 88;
29. h) M. A. Bennett, M. Bown, L. Y. Goh, D. C. R. Hockless, T. R. B. Mitchell, Organometallics 1995, 14, 1000.
30. [3a]
31. The NOE signals were observed between H4 and H6 and between H7 and H9 in 6.
32. During the reaction, a yellow precipitate of p-BPBB was generated.
33. -1, T = 133 K, 1668 variables refined with 35 196 reflections with I > 3σ(I) to R1 = 0.077. CCDC-604664 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
34. II complex in which the Pd center is largely distorted from the square-planar geometry was recently reported: C. M. Frech, L. J. W. Shimon, D. Milstein, Angew. Chem. 2005, 117, 1737;
35. Angew. Chem. Int. Ed. 2005, 44, 1709, and references therein.
36. a) Y. Yamamoto, K. Takahashi, H. Yamazaki, J. Am. Chem. Soc. 1986, 108, 2458;
37. b) P. Braunstein, M. A. Luke, New J. Chem. 1988, 12, 429;
38. c) Y. Yamamoto, H. Yamazaki, Organometallics 1993, 12, 933;
39. d) M. Rashidi, J. J. Vittal, R. J. Puddephatt, J. Chem. Soc. Dalton Trans. 1994, 1283;
40. e) T. Tanase, H. Takahata, H. Ukaji, M. Hasegawa, Y. Yamamoto, J. Organomet. Chem. 1997, 538, 247;
41. f) T. Tanase, H. Toda, Y. Yamamoto, Inorg. Chem. 1997, 36, 1571;
42. g) T. Tanase, H. Ukaji, H. Takahata, H. Toda, T. Igoshi, Y. Yamamoto, Organometallics 1998, 17, 196.
43. nPh range from 1.373 to 1.406 Å for n = 1, and 1.331 to 1.421 Å for n = 3: a) G. P. Bartholomew, X. Bu, G. C. Bazan, Chem. Mater. 2000, 12, 2311;
44. b) P. F. van Hutten, J. Wildeman, A. Meetsma, G. Hadziioannou, J. Am. Chem. Soc. 1999, 121, 5910.
45. 4-(p-divinylbenzene)}], in which the four carbon atoms in the p-phenylene moiety participate in the coordination to two Fe centers. R. E. Davis, R. Pettit, J. Am. Chem. Soc. 1970, 92, 716.
46. T. W. Campbell, R. N. McDonald, J. Org. Chem. 1959, 24, 1246.
47. The angles 150° and 120° in Scheme 5 are defined by the midpoints of the C-C bonds, such that all C-C bond lengths and C-C-C angles are fixed as being equivalent.