Highly efficient catalytic reactions via activation of a Si-H bond of organohydrosilanes by triruthenium carbonyl clusters bearing bridging an acenaphthylene or azulene ligand

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 63, Issue 2, 2005, Pages 122-133

  Matsubara, Kouki ^a   Nagashima, Hideo ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

Catalytic hydrosilylation of ketones and aldehydes; Polymerization of cyclic ethers; Polymerization of cyclic siloxanes; Polymerization of vinyl ethers; Reduction of acetals; Reduction of carboxylic acids and derivatives; Ruthenium carbonyl clusters

Indexed keywords

ACTIVATION ANALYSIS; ALDEHYDES; CARBOXYLATION; DERIVATIVES; ETHERS; KETONES; OXIDATION; POLYMERIZATION; RUTHENIUM COMPOUNDS; TRANSITION METALS;

CATALYTIC HYDROSILYLATION OF KETONES AND ALDEHYDES; HAPTICITY CHANGE OF POLYAROMATIC LIGAND; OXIDATIVE ADDITION OF A SI-H BOND; POLYMERIZATION OF CYCLIC ETHERS; POLYMERIZATION OF CYCLIC SILOXANES; POLYMERIZATION OF VINYL ETHERS; REDUCTION OF ACETALS; REDUCTION OF CARBOXYLIC ACIDS AND DERIVATIVES; RUTHENIUM CARBONYL CLUSTERS; SILYL RUTHENIUM CLUSTERS;

CATALYSIS;

EID: 17444402910     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.63.122     Document Type: Article

References (84)

1. For reviews', (a) "Comprehensive Handbook on Hydrosilylation" ed. by B. Marciniec, Pergamon Press, Oxford, 1992; (b) I. Ojima, "The Chemistry of Organosilicon Compounds" ed. by S. Patai, Z. Rappoport, Wiley, New York, 1989, p 1479; (c) J. L. Spier, Adv. Organomet. Chem., 17, 407 (1978)
2. For reviews', (a) "Comprehensive Handbook on Hydrosilylation" ed. by B. Marciniec, Pergamon Press, Oxford, 1992; (b) I. Ojima, "The Chemistry of Organosilicon Compounds" ed. by S. Patai, Z. Rappoport, Wiley, New York, 1989, p 1479; (c) J. L. Spier, Adv. Organomet. Chem., 17, 407 (1978)
3. For reviews', (a) "Comprehensive Handbook on Hydrosilylation" ed. by B. Marciniec, Pergamon Press, Oxford, 1992; (b) I. Ojima, "The Chemistry of Organosilicon Compounds" ed. by S. Patai, Z. Rappoport, Wiley, New York, 1989, p 1479; (c) J. L. Spier, Adv. Organomet. Chem., 17, 407 (1978)
4. (a) H. Nishiyama, K. Itoh, "Catalytic Asymmetric Synthesis" ed. by I. Ojima, Wiley VCH, New York, 2000, Chapter 2;
5. (b) T. E. Waldman, G. Schaefer, D. P. Riley, "Selectivity in Catalysis" ed. by M. E. Davis, S. L. Suib, ACS, Washington DC, 1993;
6. (c) H. L. Pedersen, M. Johannsen, J. Org. Chem., 67, 7982 (2002) and references cited therein
7. (a) S. C. Berk, K. A. Kreutzer, S. L. Buchwald, J. Am. Chem. Soc., 113, 5093 (1991);
8. (b) S. C. Berk, S. L. Buchwald, J. Org. Chem., 57, 3751 (1992);
9. (c) S. Bower, K. A. Kristina, S. L. Buchwald, Angew. Chem., Int. Ed. Engl., 35, 1515 (1996);
10. (d) K. J. Barr, S. C. Berk, S. L. Buchwald, J. Org. Chem., 59, 4323 (1994)
11. T. Ohta, M. Kamiya, K. Kusui, T. Michibata, M. Nobutomo, I. Furukawa, Tetrahedron Lett., 40, 6963 (1999)
12. Z. Mao, B. T. Gregg, A. R. Cutler, J. Am. Chem. Soc., 117, 10139 (1995)
13. (a) M. Igarashi, R. Mizuno, T. Fuchikami, Tetrahedron Lett., 42, 2149 (2001);
14. (b) M. Igarashi, T. Fuchikami, ibid., 42, 1945 (2001)
15. R. Kuwano, M. Takahashi, Y. Ito, Tetrahedron Lett., 39, 1017 (1998)
16. (a) S. Murai, N. Sonoda, Angew. Chem., Int. Ed. Engl., 18, 837 (1979);
17. (b) N. Chatani, S. Murai, Synlett, 1996, 414;
18. (c) I. Matsuda, A. Ogiso, S. Sato, Y. Izumi, J. Am. Chem. Soc., 111, 2332 (1989)
19. (a) M. Hudlicky, "Reductions in Organic Chemistry" Wiley, New York, 1984;
20. (b) "Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry, Vol 8, Reduction" ed. by B. M. Trost, I. Fleming, Pergamon, Oxford, 1992;
21. (c) J. Seyden-Penne, "Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd Ed" Wiley, New York, 1997
22. For example, E. Frainnet, C. Esclamadon, Compt. Rend., C254, 1814 (1962), T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett., 1979, 4679
23. For example, E. Frainnet, C. Esclamadon, Compt. Rend., C254, 1814 (1962), T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett., 1979, 4679
24. (a) A. J. Chalk, J. Chem. Soc., Chem. Commun., 1970, 847;
25. (b) J. V. Crivello, M. -X. Fan, J. Polymer Sci., Part A, 29, 1853 (1991)
26. (a) "Catalysis by Di- and Polynuclear Metal Cluster Complexes" ed. by R. D. Adams, F. A. Cotton, Wiley-VCH, Canada, 1998;
27. (b) "Metal Clusters in Chemistry" ed. by P. Braunstein, L. A. Oro, P. R. Raithby, Wiley-VCH, Weinheim, 1999
28. (a) F. Seitz, M. S. Wrighton, Angew. Chem., Int. Ed. Engl., 27, 289 (1988);
29. (b) H. Sakurai, K. Miyoshi, Y. Nakadaira, Tetrahedron Lett., 1977, 2671;
30. (c) N. Chatani, T. Komada, Y. Kajiwara, H. Murakami, F. Kakiuchi, S. Ikeda, S. Murai, Chem. Lett., 2000, 14
31. (a) I. Matsuda, A. Ogiso, S. Sato, Y. Izumi, J. Am. Chem. Soc., 111, 2332 (1989);
32. (b) I. Ojima, R. J. Donovan, N. Clos, Organometallics, 10, 2606 (1991)
33. (a) I. Matsuda, Y. Fukuta, T. Tsuchihashi, H. Nagashima, K. Itoh, Organometallics, 16, 4327 (1997);
34. (b) I. Ojima, P. Ingallina, R. J. Donovan, N. Clos, ibid., 10, 38 (1991);
35. (c) I. Ojima, R. J. Donovan, P. Ingallina, N. Clos, W. R. Shay, M. Eguchi, Q. Zeng, A. Korda, J. Cluster Sci., 3, 423 (1992);
36. (d) I. Ojima, Z. Li, R. J. Donovan, P. Ingallina, Inorg. Chim. Acta, 270, 279 (1998)
37. (a) A. N. Nesmeyanov, R. K. Friedlina, E. C. Chuskovskaya, R. G. Petrov, A. B. Belyavsky, Tetrahedron, 17, 61 (1962);
38. (b) I. Ojima, T. Fuchikami, M. Yatabe, J. Organomet. Chem., 221, C 36 (1981);
39. (c) Y. Seki, K. Takeshita, K. Kawamoto, S. Murai, N. Sonoda, J. Org. Chem., 51, 3890 (1986);
40. (d) idem, Angew. Chem., Int. Ed. Engl., 19, 928 (1980);
41. (e) H. S. Hilal, S. Khalaf, W. Jondi, J, Organomet. Chem., 452, 167 (1993)
42. (a) M. E. Rerek, F. Basolo, J. Am. Chem. Soc., 106, 5908 (1984);
43. (b) T. C. Forchner, A. R. Cutler, Kulling, R. K. Organometallics, 6, 889 (1987) and references cited therein
44. (a) H. Nagashima, T. Fukahori, K. Aoki, K. Itoh, J. Am. Chem. Soc., 115, 10430 (1993);
45. (b) H. Nagashima, A. Suzuki, M. Nobata, K. Itoh, ibid., 118, 687 (1996);
46. (c) H. Nagashima, A. Suzuki, M. Nobata, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn., 70, 2231 (1997);
47. (d) idem, ibid., 71, 2441 (1998);
48. (e) H. Nagashima, A. Suzuki, H. Kondo, M. Nobata, K. Aoki, K. Itoh, J. Organomet. Chem., 580, 239 (1999)
49. (a) H. Nagashima, T. Fukahori, M. Nobata, A. Suzuki, M. Nakazawa, K. Itoh, Organometallics, 13, 3427 (1994);
50. (b) K. Matsubara, T. Oda, H. Nagashima, ibid, 21, 881 (2001);
51. (c) K. Matsubara, S. Mima, T. Oda, H. Nagashima, J. Organomet. Chem., 650, 96 (2002)
52. H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics, 19, 3579 (2000)
53. (a) I. Ojima, T. Kogure, Organometallics, 1, 1390 (1982);
54. (b) R. N. Misra, M. F. Semmelhack, J. Org. Chem., 47, 2689 (1982);
55. (c) Recent example; G. Z. Zheng, T. H. Chan, Organometallics, 14, 70 (1995) and references cited therein
56. M. D. Cavanaugh, B. T. Gregg, A. R. Cutler, Organometallics, 15, 2764 (1996)
57. (a) H. Nagashima, K. Tatebe, T. Ishibashi, A. Nakaoka, J. Sakakibara, K. Itoh, Organometallics, 14, 2868 (1995);
58. (b) H. Nagashima, K. Tatebe, T. Ishibashi, J. Sakakibara, K. Itoh, ibid, 8, 2495 (1989)
59. K. Matsubara, T. Iura, T. Maki, J. Terasawa, H. Nagashima, The Reports of Adv. Material Study, Kyushu Univ., 15, 183 (2001)
60. (a) K. Matsubara, T. Iura, T. Maki, H. Nagashima, J. Org. Chem., 67, 4985 (2002);
61. (b) Y. Motoyama, C. Itonaga, T. Ishida, M. Takasaki, H. Nagashima, sbumitted to Org. Syn.
62. T. Iura, K. Matsubara, H. Nagashima, The Reports of Adv. Material Study, Kyushu Univ., 14, 119 (2000)
63. M. Takaki, R. Asami, T. Kuwabara, Polymer Bulletin, 7, 521 (1982)
64. A. Kajiwara, K. Matyjaszewski, Macromolecules, 31, 3489 (1998)
65. M. Narita, R. Nomura, T. Endo, Macromolecules, 31, 2774 (1998) and references cited therein
66. K. Matsubara, J. Terasawa, H. Nagashima, J. Organomet. Chem., 660, 14 5(2002)
67. (a) B. Suryanarayanan, B. W. Peace, K. G. Mayhan, J. Polym. Sci. Polym. Chem. Ed, 12, 1089 (1974);
68. (b) idem, ibid., 12, 1109 (1974);
69. (c) M. Murano, Y. Li, Y. Kawakami, Macromolecules, 33, 3940 (2000)
70. H. Nagashima, C. Itonaga, J. Yasuhara, Y. Motoyama, K. Matsubara, Organometallics, 23, 5779 (2004)
71. K. Matyjaszewski, M. Sawamoto, "Cationic Polymerizations: Mechanisms, Synthesis, and Applications" ed. by K. Matyjaszewski, Marcel Dekker, New York, 1996
72. J. V. Crivello, M. -X. Fan, J. Polym. Sci. Part A, 29, 1853 (1991)
73. As a related work, polymerization of vinyl ether by catalysis of platinum salts and hydrosilanes was briefly mentioned in a patent; J. V. Crivello, M. -X. Fan, USP, 5 272 233 (1993)
74. J. V. Crivello, S. K. Rajaraman, Tetrahedron, 53, 15167 (1997)
75. (a) D. W. Ovenall, Macromolecules, 17, 1458(1983);
76. (b) H. Ohgi, T. Sato, Polymer, 43, 3829 (2002)
77. K. Matsubara, K. Ryu, T. Maki, T. Iura, H. Nagashima, Organometallics, 21, 3023 (2002)
78. (a) M. S. Gong, H. K. Hall, Macromolecules, 19, 3011 (1986);
79. (b) J. S. Hrkach, K. Matyjaszewski, ibid, 25, 2070 (1992), C.-H. Lin, K. Matyjaszewski, J. Polymer Sci.: Part A, 28, 1771 (1990);
80. (b) J. S. Hrkach, K. Matyjaszewski, ibid, 25, 2070 (1992), C.-H. Lin, K. Matyjaszewski, J. Polymer Sci.: Part A, 28, 1771 (1990);
81. (c) G. A. Olah, Q. Wang, X. Li, G. Rasul, G. K. S. Prakash, Macromolecules, 29, 1858 (1996)
82. T. Murai, E. Yasui, S. Kato, Y. Hatayama, S. Suzuki, Y. Yamasaki, N. Sonoda, H. Kurosawa, Y. Kawasaki, S. Murai, J. Am. Chem. Soc., 111, 7938 (1989)