Novel metallacycle complexes from bis(oxazolinyl)pyridine-rhodium(I) species and diynes

Organometallics

Volumn 21, Issue 13, 2002, Pages 2572-2574

  Nishiyama, Hisao ^a   Niwa, Eiko ^a   Inoue, Tomohiro ^a   Ishima, Yosuke ^a   Aoki, Katsuyuki ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

CATALYST ACTIVITY; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RHODIUM; X RAY CRYSTALLOGRAPHY;

ORGANIC COMPOUNDS;

EID: 0038006281     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0202221     Document Type: Article

References (44)

1. For rhodacyclopentadienes and rhodium-catalyzed cyclotrimerization of alkynes, see the following. Review: (a) Müller, E. Synthesis 1974, 761. The related rhodacycles
2. (b) Igresias, M.; del Pino, C.; Ros, J.; Blanco, S, G.; Carrera, S. M. J. Organomet. Chem. 1988, 338, 89.
3. (c) Bianchini, C.; Masi, D.; Meli, A.; Peruzzini, M.; Vacca, A.; Laschi, F.; Zanello, P. Organometallics 1991, 10, 636.
4. (d) Bianchini, C.; Meli, A.; Perzzini, M.; Vacca, A.; Vizza, F. Organometallics 1991, 10, 645. The related catalysis;
5. (e) Abdulla, K.; Booth, B. L.; Stacy, C. J. Organomet. Chem. 1985, 293, 103.
6. (f) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357.
7. (g) Amer, I.; Bernstein, T.; Eisen, M.; Blum, J.; Peter, K.; Vollhardt, K. P. C. J. Mol. Catal. 1990, 60, 313.
8. (h) Ceccon, A.; Gambaro, A.; Santi, S.; Venzo, A. J. Mol. Catal. 1991, 69, L1.
9. (i) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605.
10. (j) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561.
11. (k) Witulski, R.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426.
12. General reviews of alkyne cyclotrimerization: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
13. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1129.
14. (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.
15. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
16. (e) Malacria, M. Chem. Rev. 1996, 96, 289.
17. (f) Bönnemann, H.; Brjoux, W. Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds; Wiley-VCH: Weinheim, Germany, 1998; Vol. l, p 114.
18. For metallacycles of other transition metals, see the following. For Ir: (a) Collman, J. P.; Kang, J. W.; Little, W. F.; Sullivan, M. F. Inorg. Chem. 1988, 7, 1298.
19. (b) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145.
20. (c) O'Connor, J. M.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 6232.
21. (d) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, S. A.; Johnson, T. J.; Meli, A.; Peruzzuni, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
22. (e) O'Connor, J. M.; Merwin, R.; Rheingold, A. L.; Adams, M. L. Organometallics 1998, 14, 2102.
23. (f) Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem. 1999, 52, 1085.
24. (g) O'Connor, J. M.; Closson, A.; Hiibner, K.; Merwin, R.; Gantzel, P.; Roddick, D. M. Organometallics 2001, 20, 3710.
25. (h) O'Connor, J. M.; Closson, A.; Gantzel, P. J. Am. Chem. Soc. 2002, 124, 2434.
26. The related cyclotrimerization: (i) Takeuchi, R.; Tanaka, S.; Nakaya, Y. Tetrahedron Lett. 2001, 42, 2991.
27. For Ni: (j) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133.
28. (k) Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231.
29. (l) Mori, N.; Ikeda, S.; Odashima, K. Chem. Commun. 2001, 181.
30. For Pd: (m) Yamamoto, Y.; Nagata, A.; Itoh, K. Tetrahedron Lett. 1999, 40, 5035.
31. For Ru: (n) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549.
32. (o) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965.
33. (a) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
34. (b) Nishiyama, H.; Naitoh, T.; Motoyama, Y.; Aoki, K. Chem. Eur. J. 1999, 5, 3509.
35. (c) Iwasa, S.: Takezawa, F.; Tuchiya, Y.; Nishiyama, H. Chem. Commun. 2001, 59.
36. (d) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron 2002, 58, 227.
37. (a) Nishiyama, H.; Horihata, M.; Hirai, T.; Wakamatsu, S.; Itoh, K. Organometallics 1991, 10, 2706. Related papers for tridentate nitrogen-ligand-Rh(I) species
38. (b) Haarman, H. F.; Ernsting, J. M.; Kranenburg, M.; Kooijman, H.; Veldman, N.; Spek, A. L.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1997, 16, 887.
39. (c) Nückel, S.; Burger, P. Organometallics 2001, 20, 4359.
40. w= 5.0%. The Cambridge Crystallographic Database file is CCDC-178534.
41. (a) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, K.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310.
42. (b) Rüba, E.; Mereiter, K.; Schmid, R.; Kirchiner, K. Chem. Commun. 2001, 1996 and references therein.
43. w = 8.0%. The Cambridge Crystallographic Database file is CCDC-178535.
44. For a new observation of metallacyclopentadiene cobalt complexes and their related reactions in terms of reaction mechanism for cyclotrimerization, see: Diercks, R.; Eaton, B. E.; Gürtzgen, S.; Jalisatgi, S.; Matzger, A. J.; Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247.