Systematic evaluation of substituted cyclopentadienyl ruthenium complexes, [(η5-C5MeNH5N) RuCl(cod)], for catalytic cycloadditions of diynes

Chemistry - An Asian Journal

Volumn 5, Issue 4, 2010, Pages 946-952

  Yamamoto, Yoshihiko ^a   Yamashita, Ken ^a   Harada, Yu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Cycloaddition; Cyclopentadienyl ligand; Cyclopropanation; Diyne; Ruthenium catalyst

Indexed keywords

CATALYST LOADINGS; CATALYTIC PERFORMANCE; CHEMO-SELECTIVITY; CYCLOADDITIONS; CYCLOPENTADIENYL LIGANDS; CYCLOPENTADIENYLS; CYCLOPROPANATION; DIYNE; EFFICIENT CATALYSTS; ELECTRON DENSITIES; ELECTRONIC EFFECTS; H NMR SPECTROSCOPY; INITIAL RATE; NORBORNENES; RUTHENIUM CATALYSTS; RUTHENIUM COMPLEXES; SYSTEMATIC EVALUATION; TURNOVER NUMBER; UNSYMMETRICAL; VOLTAMMETRIC ANALYSIS;

ACETYLENE; CATALYSTS; CYCLOADDITION; LIGANDS; LIGHTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM;

RUTHENIUM COMPOUNDS;

EID: 77950839859     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900531     Document Type: Article

References (53)

1. For reviews, see: a) S. Derien, P. H. Dixneuf, J. Organomet. Chem. 2004, 689, 1382-1392;
2. B. M. Trost, M. U. Frederiksen, M. T. Rudd, Angew. Chem. 2005, 117, 6788-6825;
3. Angew. Chem. Int. Ed. 2005, 44, 6630-6666;
4. M. Ito, T. Ikariya, Chem. Commun. 2007, 5134-5142;
5. M. Kamigaito, T. Ando, M. Sawamoto, Chem. Rec. 2004, 4, 159-175;
6. H. Suzuki, Eur. J. Inorg. Chem. 2002, 1009-1023;
7. M. Jimenez-Tenorio, M. C. Puerta, P. Valerga, Eur. J. Inorg. Chem. 2004, 17-32;
8. M. O. Albers, D. J. Robinson, E. Singleton, Coord. Chem. Rev. 1987, 79, 1-96.
9. *, and Ind, see: a) B. M. Trost, B. Vidal, M. Thommen, Chem. Eur. J. 1999, 5, 1055-1069;
10. Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405-10406;
11. K. Onitsuka, H. Okuda, H. Sasai, Angew. Chem. 2008, 120, 1476-1479;
12. Angew. Chem. Int. Ed. 2008, 47, 1454-1457;
13. B. Martín-Matute, M. Edin, K. Bogár, F. B. Kaynak, J.-E. Bäckvall, J. Am. Chem. Soc. 2005, 127, 8817-8825;
14. B. Martín-Matute, K. Bogár, M. Edin, F. B. Kaynak, J.-E. Bäckvall, Chem. Eur. J. 2005, 11, 5832-5842;
15. B. Dutta, R. Scopelliti, K. Severin, Organomet al.lics 2008, 27, 423-429.
16. For an excellent review of ring substituent steric effects, see: P. C Möhring, N. J. Coville, Coord. Chem. Rev. 2006, 250, 18-35.
17. For a review, see: P. J. Chirik, Dalton Trans. 2007, 16-25.
18. a) Y. Yamamoto, H. Kitahara, R. Ogawa, H. Kawaguchi, K. Tatsumi, K. Itoh, J. Am. Chem. Soc. 2000, 122, 4310-4319;
19. Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143-12160;
20. Y. Yamamoto, K. Kinpara, T. Saigoku, H. Nishiyama, K. Itoh, Org. Biomol. Chem. 2004, 2, 1287-1294;
21. Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 9625-9631;
22. Y. Yamamoto, J. Ishii, H. Nishiyama, Tetrahedron 2005, 61, 11501-11510;
23. Y. Yamamoto, K. Hattori, J. Ishii, H. Nishiyama, Tetrahedron 2006, 62, 4294-4305.
24. a) D. D. Young, R. S. Senaiar, A. Deiters, Chem. Eur. J. 2006, 12, 5563-5568;
25. R. S. Senaiar, J. A. Teske, D. D. Young, A. Deiters, J. Org. Chem. 2007, 72, 7801-7804;
26. D. D. Young, L. Sripada, A. Deiters, J. Comb. Chem. 2007, 9, 735-738;
27. J. A. Teske, A. Deiters, Org. Lett. 2008, 10, 2195-2198;
28. J. A. Varela, S. G. Rubin, C. Gonzalez-Rodriguez, L. Castedo, C. Saá, J. Am. Chem. Soc. 2006, 128, 9262-9263;
29. J. A. Varela, S. G. Rubín, L. Castedo, C. Saá, J. Org. Chem. 2008, 73, 1320-1332;
30. S. García-Rubín, J. A. Varela, L. Castedo, C. Saá, Chem. Eur. J. 2008, 14, 9772-9778;
31. S. García-Rubín, J. A. Varela, L. Castedo, C. Saá, Org. Lett. 2009, 11, 983-986.
32. For recent reviews of [2+2+2] cycloadditions, see: a) B. R. Galan, T. Rovis, Angew. Chem. 2009, 121, 2870-2874;
33. Angew. Chem. Int. Ed. 2009, 48, 2830-2834;
34. P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307-2327;
35. N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, M. Malacria, Org. React. 2007, 68, 1-302;
36. S. Kotha, E. Brahmachary, K. Lahiri, Eur. J. Org. Chem. 2005, 4741-4767;
37. Y. Yamamoto, Curr. Org. Chem. 2005, 9, 503-519.
38. a) Y. Yamamoto, K. Hattori, H. Nishiyama, J. Am. Chem. Soc. 2006, 128, 8336-8340;
39. Y. Yamamoto, K. Yamashita, T. Hotta, T. Hashimoto, M. Kikuchi, H. Nishiyama, Chem. Asian J. 2007, 2, 1388-1399;
40. Y. Yamamoto, K. Hattori, Tetrahedron 2008, 64, 847-855;
41. Y. Yamamoto, R. Takuma, T. Hotta, K. Yamashita, J. Org. Chem. 2009, 74, 4324-4328.
42. 5-n) RuCl (cod), were obtained by the reported procedures: a) N. Oshima, H. Suzuki, Y. Moro-oka, Chem. Lett. 1984, 1161-1164;
43. G. O. Nelson, C. E. Sumner, Organomet al.lics 1986, 5, 1983-1990;
44. A. P. Humphries, S. A. R. Knox, J. Chem. Soc. Dalton Trans. 1 1975, 1710-1714;
45. T. Blackmore, J. D. Cotton, M. I. Bruce, F. G. A. Stone, J. Chem. Soc. A 1968, 2931-2936;
46. H. Nagashima, K. Mukai, Y. Shiota, K. Yamaguchi, K. Ara, T. Fukahori, H. Suzuki, M. Akita, Y. Moro-oka, K. Itoh, Organomet al.lics 1990, 9, 799-807;
47. H. Nagashima, K. Yamaguchi, K. Mukai, K. Itoh, J. Organomet. Chem. 1985, 291, c20-c22;
48. P. Alvarez, J. Gimeno, E. Lastra, S. Garcia-Granda, J. F. Van der Maelen, M. Bassetti, Organomet al.lics 2001, 20, 3762-3771;
49. R. Yoshizawa, T. Matsukawa, M. Takahashi (Chisso), Jpn. Kokai Tokkyo Koho 7 252168, 1995;
50. K. Katoh, K. Tsukamoto (Mitsui Chemicals), Jpn. Kokai Tokkyo Koho 10 130192, 1998.
51. For reviews, see: a) F. Basolo, Inorg. Chim. Acta 1981, 50, 65-70;
52. F. Basolo, Inorg. Chim. Acta 1985, 100, 33-39;
53. J. M. O'Connor, C. P. Casey, Chem. Rev. 1987, 87, 307-318.