Generation of metallacyclic structures from the reactions of vinyl ethers with a TpMe2IrIII compound

Organometallics

Volumn 27, Issue 23, 2008, Pages 6353-6359

  Paneque, Margarita ^a   Poveda, Manuel L ^a   Santos, Laura L ^a   Carmona, Ernesto ^a   Mereiter, Kurt ^b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ALKYLATION; CRYSTALLOGRAPHY; ETHERS; IRIDIUM; LIGANDS; MOLECULES; OPERATING ROOMS; ORGANIC COMPOUNDS; X RAY CRYSTALLOGRAPHY;

ALKOXIDE; BOND CLEAVAGES; C-H ACTIVATIONS; CARBENE; DIANIONIC LIGANDS; ORGANIC LIGANDS; VINYL ETHERS; X-RAY CRYSTALLOGRAPHIES;

COORDINATION REACTIONS;

EID: 57849117971     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800844x     Document Type: Article

References (81)

1. (a) Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999.
2. (b) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
3. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
4. (d) Pamplin, C. B.; Legzdins, P. Acc. Chem. Res. 2003, 46, 223.
5. (e) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
6. (f) Blackmore, I. J.; Jin, X.; Legzdins, P. Organometallics 2005, 24, 4088.
7. (a) Bergman, R. G. Nature 2007, 446, 391.
8. (b) Perutz, R. N.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2007, 46, 2678.
9. For example, see: (a) Cowan, A. J.; Portins, P.; Kawanami, H. K.; Jina, O. S.; Grills, D. C.; Sun, X.-Z.; Mc Master, J.; George, M. W. Proc Natl. Acad. Sci. U.S.A. 2007, 104, 6933.
10. (b) Cobar, E. A.; Khaliullin, R. Z.; Bergman, R. G.; Head-Gordon, M. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6963.
11. (a) Catalysis: An Integrated Approach to Homogeneous, Heterogeneous, and Industrial Catalysis; Moulijn, J. A., van Leeuwen, P. W. N. M., van Santen, R. A., Eds.; Elsevier: Amsterdam, The Netherlands, 1993.
12. (b) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
13. (c) Activation and Functionalization of C-H Bonds; Goldberg, K. I., Golman, A. S., Eds.; ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004.
14. (d) Conley, B.; Tenn, W. I.; Young, K. J. H.; Ganesh, S.; Meier, S.; Oxgaard, J.; Gonzales, J.; Goddard, W. A., III.; Periana, R. A. In Activation of Small Molecules; Tolman, W. B., Ed.; Wiley-VCH: Weinheim, Germany, 2006; Chapter 7.
15. (a) Kirfflova, M. V.; Kuznetsov, M. L.; Reis, P. M.; da Silva, J. A. L.; Frausto da Silva, J. J. R.; Pombeiro, A. J. L. J. Am. Chem. Soc. 2007, 129, 10531.
16. (b) Chen, M. S.; White, M. C. Science 2007, 318, 783.
17. (c) Jones, C. J.; Taube, D.; Ziatdinov, V. R.; Periana, R. A.; Nielsen, R. J.; Oxgaard, J.; Goddard, W. A., III. Angew. Chem., Int. Ed. 2004, 43, 4626.
18. (a) Elschenbroich, C. Organometallics; Wiley-VCH: Weinheim, Germany, 2006.
19. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
20. (c) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
21. (d) Foley, N. A.; Lail, M.; Lee, J. P.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2007, 129, 6765.
22. For some selected examples, see: (a) West, N. M.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 2007, 129, 12372.
23. (b) Bradley, C. A.; Veiros, L. F.; Pun, D.; Lobkovsky, E.; Keresztes, I.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 16600.
24. (c) Ozerov, O. V.; Pink, M.; Watson, L. A.; Caulton, K. G. J. Am. Chem. Soc. 2004, 126, 2105.
25. (d) Clot, E.; Chen, J.; Lee, D.-H.; Sung, S. Y.; Appelhans, L. N.; Faller, J. W.; Crabtree, R. H.; Eisenstein, O. J. Am. Chem. Soc. 2004, 126, 8795.
26. (e) Goj, L. A.; Lail, M.; Pittard, K. A.; Riley, K. C.; Gunnoe, T. B.; Petersen, J. L. Chem. Commun. 2006, 982.
27. For examples from this laboratory, see: (a) Slugovc, C.; Mereiter, K.; Trofimenko, S.; Carmona, E. Angew. Chem., Int. Ed. 2000, 39, 2158.
28. (b) Santos, L. L.; Mereiter, K.; Paneque, M.; Slugovc, C.; Carmona, E. New J. Chem. 2003, 27,107.
29. (c) Carmona, E.; Paneque, M.; Poveda, M. L. Dalton Trans. 2003, 4022.
30. (d) Carmona, E.; Paneque, M.; Santos, L. L.; Salazar, V. Coord. Chem. Rev. 2005, 249, 1729.
31. (a) Caldwell, T. E.; Abdelrehim, I. M.; Land, D. P. J. Am. Chem. Soc. 1996, 118, 907.
32. (b) Furimsky, E. Catal. Rev. Sci. Eng. 1983, 25, 421.
33. (a) Weissman, H.; Shimon, L. J. W.; Milstein, D. Organometallics 2004, 23, 3931.
34. (b) Van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 6531.
35. (c) Ferrando, G.; Coalter, J. N., III.; Gerard, H.; Huang, D.; Eisenstein, O.; Caulton, K. G. New J. Chem. 2003, 27, 1451.
36. (a) Arnold, J.; Tilley, T. D. J. Am. Chem. Soc. 1985, 107, 6409.
37. (b) Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
38. (c) Van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Vigalok, A.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 625.
39. (d) Chataui, N.; Tatamidani, H.; Ie, Y.; Kakinchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 4849.
40. (e) Grotjahn, D. B.; Lo, H. C. Organometallics 1996, 15, 2860.
41. (f) Mayer, J. M. Polyhedron 1995, 14, 3273.
42. (a) Lin, Y.-S.; Yamamoto, A. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; pp 161 - 192.
43. (b) Baumann, R.; Stumpf, R.; Davis, W. M.; Liang, L.-Ch.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 7822.
44. (c) Tolman, C. A.; Ittel, S. D.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1979, 101, 1742.
45. (d) Yamamoto, Y.; Sato, R.; Matsuo, F.; Sudoh, C.; Igoshi, T. Inorg. Chem. 1996, 35, 2329.
46. (e) Empsall, H. D.; Hyde, E. M.; Jones, C. H.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1974, 1980.
47. Lara, P.; Paneque, M.; Povieda, M. L.; Salazar, V.; Santos, L. L.; Carmona, E. J. Am. Chem. Soc. 2006, 128, 3512.
48. Alvarez, E.; Paneque, M.; Petronilho, A. G.; Povieda, M. L.; Santos, L. L.; Carmona, E.; Mereiter, K. Organometallics 2007, 26, 1231.
49. (a) da Silva, G.; Kim, C.-H.; Bozzelli, J. W. J. Phys. Chem. A 2006, 110, 7925.
50. (b) Prashad, M.; Lu, Y.; Repic, O. J. Org. Chem. 2004, 69, 584.
51. (c) Thiault, G.; Thévenet, R.; Le Bras, G. Phys. Chem. Chem. Phys. 2002, 4, 613.
52. (a) Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1993, 115, 554.
53. (b) Jones, W. D. Inorg. Chem. 2005, 44, 4475.
54. (a) Stoutland, P. O.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. Polyhedron 1988, 7, 1429.
55. (b) Uddin, J.; Morales, C. M.; Maynard, J. H.; Landis, C. R. Organometallics 2006, 25, 5566.
56. Alvarado, Y.; Bountry, O.; Gutiérrez, E.; Monge, A.; Nicasio, M. C.; Poveda, M. L.; Pérez, P. J.; Ruiz, C.; Bianchini, C.; Carmona, E. Chem. - Eur. J. 1997, 3, 860.
57. Gutiérrez-Puebla, E.; Monge, A.; Nicasio, M. C.; Poveda, M. L.; Pérez, P. J.; Carmona, E. Chem.-Eur. J. 1998, 4, 2225.
58. (a) Werner, H.; Werber, B.; Nürnberg, O.; Wolf, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1025.
59. (b) Clark, G. R.; Roger, W. R.; Wright, A. H. J. Organomet. Chem. 1982, 236, C7.
60. See, for example, p 338 of ref 6a.
61. (a) Paneque, M.; Posadas, C. M.; Poveda, M. L.; Rendón, N.; Alvarez, E.; Mereiter, K. Chem.-Eur. J. 2007, 13, 5160.
62. (b) Paneque, M.; Posadas, C. M.; Poveda, M. L.; Rendon, N.; Mereiter, K. Organometallics 2007, 26, 3120.
63. (c) Gandon, V.; Agenet, N.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. J. Am. Chem. Soc. 2006, 128, 8509.
64. (d) Nishiyama, H.; Niwa, E.; Inoue, T.; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572.
65. General reviews of alkyne cyclotrimerization:(a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
66. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1129.
67. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 741.
68. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
69. (e) Malacria, M. Chem. Rev. 1996, 96, 289.
70. (f) Bönnemann, H.; Brijoux, W. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, p 114.
71. O'Connor, J. M.; Closson, A.; Gantzel, P. J. Am. Chem. Soc. 2002, 124, 2434.
72. (a) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
73. (b) Herberich, G. E.; Mayer, H. Organometallics 1990, 9, 2655.
74. (c) Yeh, W. Y.; Peng, S. M.; Liu, L. K. Inorg. Chem. 1993, 32, 2965.
75. (a) Alías, F. M.; Daff, P. J.; Paneque, M.; Poveda, M. L.; Carmona, E.; Pérez, P. J.; Salazar, V.; Alvarado, Y.; Atencio, R.; Sánchez-Delgado, R. Chem.-Eur. J. 2002, 8, 5132.
76. (b) Bodner, G. S.; Smith, D. E.; Harton, W. G.; Heah, P. C.; Georgiou, S.; Rheingold, A. L.; Geib, S. J.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 109, 7688.
77. (c) Feng, S. G.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1992, 114, 2951.
78. (d) Zhen, H.; Wang, C.; Hu, Y.; Rood, T. C. Organometallics 1998, 17, 5397.
79. Bruker programs: SMART, version 5.629; SAINT+, version 6.45; SADABS, version 2.10; SHELXTL, version 6.14; Bruker AXS Inc.: Madison, WI, 2003.
80. Sheldrick, G. M. SHELX97: Program System for Crystal Structure Determination; University of Göttingen: Göttingen, Germany.
81. Spek, A. L. PLATON: A Multipurpose Crystallography Tool; University of Utrecht, Utrecht, The Netherlands, 2008.