Ruthenium-cluster-mediated activation of all bonds of a methyl group of 6,6′-dimethyl-2,2′-bipyridine and 2,9-dimethyl-1,10- Phenanthroline: Transformation of the latter into a 2-alkenyl-9-methyl-1,10- phenanthroline ligand

Chemistry - A European Journal

Volumn 12, Issue 5, 2006, Pages 1529-1538

  Cabeza, Javier A ^a   Del Río, Ignacio ^a   Martínez Mendez, Lorena ^a   Migue, Daniel ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

C C activation; C H activation; Cluster compounds; N ligands; Ruthenium

Indexed keywords

AROMATIC COMPOUNDS; CARBON; CHEMICAL ANALYSIS; RUTHENIUM; THERMAL EFFECTS;

C-C ACTIVATION; C-H ACTIVATION; CLUSTER COMPOUNDS; N LIGANDS;

CHEMICAL BONDS;

EID: 32044448930     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500813     Document Type: Article

References (70)

1. For selected reviews on C-H bond activation, see: a) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507;
2. b) B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154;
3. c) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879;
4. d) W. D. Jones, in Topics in Organometallic Chemistry: Activation of Unreactive Bonds and Organic Synthesis (Ed. : S. Murai), Springer, Heidelberg, 1999, p. 9;
5. e) G. Dyker, Angew. Chem. 1999, 111, 1808;
6. Angew. Chem. Int. Ed. 1999, 35, 1699;
7. f) Y. Guari, S. Sabo-Etienne, B. Chaudret, Eur. J. Inorg. Chem. 1999, 1047.
8. For selected reviews on C-C bond activation, see: a) B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918;
9. Angew. Chem. Int. Ed. 1999, 38, 870;
10. b) M. Murakami, Y. Ito, in Topics in Organometallic Chemistry: Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, Heidelberg, 1999, p. 97.
11. See, for example: a) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
12. b) C.-H. Jun, C. W. Moon, D.-Y. Lee, Chem. Eur. J. 2002, 8, 2423;
13. c) A. E. Shilov, G. B. Shul'pin, Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes, Kluwer, Dordrecht, 2000;
14. d) A. Sen, Acc. Chem. Res. 1998, 31, 550;
15. e) F. Kakiuchi, S. Murai in Topics in Organometallic Chemistry: Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, Heidelberg, 1999, p. 47.
16. B. Breit, Chem. Eur. J. 2000, 6, 1519.
17. a) J. A. Cabeza, I. del Río, P. García-Alvarez, V. Riera, M. Suárez, S. García-Granda, Dalton Trans. 2003, 2808;
18. b) J. A. Cabeza, I. del Río, P. García-Alvarez, D. Miguel, V. Riera, Inorg. Chem. 2004, 43, 5450.
19. J. A. Cabeza, I. del Río, V. Riera, M. Suárez, S. García-Granda, Organometallics 2004, 23, 1107.
20. A preliminary communication of part of this work has been reported: J. A. Cabeza, I. da Silva, I. del Río, L. Martínez-Méndez, D. Miguel, V. Riera, Angew. Chem. 2004, 116, 3546;
21. Angew. Chem. Int. Ed. 2004, 43, 3464.
22. a) T. Venäläinen, J. Pursiainen, T. A. Pakkanen, J. Chem. Soc. Chem. Commun. 1985, 1348;
23. b) M. I. Bruce, M. G. Humphrey, M. R. Snow, E. R. T. Tiekink, R. C. Wallis, J. Organomet. Chem. 1986, 374, 311.
24. J. A. Cabeza, L. A. Oro, A. Tiripicchio, M. Tiripicchio-Camellini, J. Chem. Soc. Dalton Trans. 1988, 1437.
25. M. Gandelman, L. J. W. Shimon, D. Milstein, Chem. Eur. J. 2003, 9, 4295, and references therein.
26. a) M. P. Cifuentes, T. P. Jeynes, M. G. Humphrey, B.W. Skelton, A. H. White, J. Organomet. Chem. 1995, 494, 267;
27. b) W.-Y. Yeh, Y.-C. Liu, S.-M. Peng, G.-H. Lee, Organometallics 2003, 22, 2361;
28. c) J. A. Bandy, M. L. H. Green, D. O'Hare, J. Chem. Soc. Dalton Trans. 1986, 2477;
29. d) J. R. Shapley, M. Tachikawa, M. R. Churchill, R. A. Lashewycz, J. Organomet. Chem. 1978, 162, C39;
30. e) R. Zoet, G. van Koten, K. Vrieze, J. Jansen, K. Goubitz, C. H. Stam, Organometallics 1988, 7, 1565;
31. f) M. Akther, K. A. Azam, S. E. Kabir, K. M. A. Malik, R. Mann, Polyhedron 2003, 22, 355;
32. g) S. E. Kabir, M. Day, M. Irving, T. McPhillips, H. Minassin, E. Rosenberg, K. I. Hardcastle, Organometallics 1991, 10, 3997;
33. h) M. Day, W. Freeman, K. I. Hardcastle, M. Isomaki, S. E. Kabir, T. McPhillips, E. Rosenberg, L. G. Scot, E. Wolf, Organometallics 1992, 11, 3376;
34. i) R. D. Adams, G. Chen, Y. Chi. Organometallics 1992, 11, 1473.
35. a) A. Herzog, H.W. Roesky, F. Jager, A. Steiner, M. Noltemeyer, Organometallics 1996, 15, 909;
36. b) A. Herzog, H. W. Roesky, Z. Zak, M. Noltemeyer, Angew. Chem. 1994, 106, 1052;
37. Angew. Chem. Int. Ed. Engl. 1994, 33, 967;
38. c) R. Andrés, P. Gómez-Sal, E. de Jésus, A. Martín, M. Mena, C. Yélamos, Angew. Chem. 1997, 109, 72;
39. Angew. Chem. Int. Ed. Engl. 1997, 36, 115;
40. d) R. Andres, M. V. Galakhov, A, Martín, M. Mena, C. Santamaría, J. Chem. Soc. Chem. Commun. 1995, 551;
41. e) D. S. Richeson, S.-H. Hsu, N. H. Fredd, G. V. Duyne, H. K. Theopold, J. Am. Chem. Soc. 1986, 108, 8273.
42. a) R. D. Adams, G. Chen, J. Cluster Sci. 1991, 2, 29;
43. b) C. G. J. Tazelaar, S. Bambirra, D. van Leusen, A. Meetsma, B. Hessen, J. H. Teuben, Organometallics 2004, 23, 936;
44. c) M. Day, S. Hajela, S. E. Kabir, M. Irving, T. McPhillips, E. Wolf, K. I. Hardcastle, E. Rosenberg, L. Milone, R. Gobetto, D. Osella, Organometallics 1991, 70, 2743;
45. d) J. A. Cabeza I. del Río, D. Miguel, M. G. Sánchez-Vega, Chem. Commun. 2005, 3956.
46. K. K. H. Lee, W. T. Wong, J. Chem. Soc. Dalton Trans. 1996, 1707.
47. R. D. Adams, J. E. Babin, M. Tasi, Organometallics 1988, 7, 503.
48. a) J. E. Kickham, F. Guérin, J. C. Stewart, D. W. Stephan, Angew. Chem. 2000, 112, 3406;
49. Angew. Chem. Int. Ed. 2000, 39, 3263;
50. b) J. E. Kickham, F. Guérin, J. C. Stewart, E. Urbanska, D. W. Stephan, Organometallics 2001, 20, 1175.
51. 4-carbyne ligands, see: a) M. J. Fernández, B. F. G. Johnson, J. Lewis, P. R. Raithby, Acta Crystallogr. Sect. B 1978, 34, 3086;
52. b) M. Miekuz, P. Bougeard, R. Faggiani, C. J. L. Lock, M. J. McGlinchey, G. Jaouen, Organometallics 1985, 4, 2046;
53. c) J. S. Bradley, G. B. Ansell, E. W. Hill, J. Am. Chem. Soc. 1979, 101, 7417;
54. d) S. Haak, A. Neels, H. Stoeckli-Evans, G. Süss-Fink, Inorg. Chem. Commun. 1999, 2, 60;
55. e) J. Wang, A. M. Crespi, M. Sabat, S. Harris, C. Woodcock, D. F. Shriver, Inorg. Chem. 1989, 28, 697;
56. f) O. Steigelmann, P. Bissinger, H. Schmidbaur, Z. Naturforsch. B 1993, 48, 72;
57. g) F. Sherbaum, B. Huber, G. Muller, H. Schmidbaur, Angew. Chem. 1988, 100, 1600;
58. Angew. Chem. Int. Ed. Engl. 1988, 27, 1542;
59. h) H. Adams, L. V. Y. Guio, M. J. Morris, S. E. Spey, J. Chem. Soc. Dalton Trans. 2002, 2907;
60. i) D. L. Davies, J. C. Jeffery, D. Miguel, P. Sherwood, F. G. A. Stone, J. Chem. Soc. Chem. Commun. 1987, 454.
61. a) R. M. Gauvin, H. Rozenberg, L. J. W. Shimon, D. Milstein, Organometallics 2001, 20, 1719;
62. b) M. Gandelman, A. Vigalok, L.J.W. Shimon, D. Milstein, Organometallics 1997, 16, 3981;
63. c) B. Rybtchinski, S. Oevers, M. Montag, A. Vigalok, H. Rozenberg, J. M. L. Martin, D. Milstein, J. Am. Chem. Soc. 2001, 123, 9064;
64. d) R. F. R. Jazzar, S. A. Macgregor, M. F. Mahon, S. P. Richards, M. K. Whittlesey, J. Am. Chem. Soc. 2002, 124, 4944.
65. 2 = 0.3345 (all data). Additional crystallo-graphic data can be obtained from the authors upon request.
66. A. G. Orpen, J. Chem. Soc. Dalton Trans. 1980, 2509.
67. SAINT+. SAX Area Detector Integration Program, version 6.02, Bruker AXS Inc., Madison, WI, 1999.
68. G. M. Sheldrick, SHELXTL, an Integrated System for Solving, Refining, and Displaying Crystal Structures from Diffraction Data, version 5.1, Bruker AXS Inc., Madison, WI, 1998.
69. G. M. Sheldrick, SADABS, Empirical Absorption Correction Program, University of Göttingen, Göttingen, Germany, 1997.
70. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, University of Göttingen, Göttingen, Germany, 1997.