Aqueous polymerization of styrene promoted by water-soluble robust ruthenium hydride complexes

Organometallics

Volumn 23, Issue 12, 2004, Pages 3047-3052

  Ogo, Seiji ^a   Uehara, Keiji ^a   Abura, Tsutomu ^a   Watanabe, Yoshihito ^b   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; HYDRIDES; INFRARED SPECTROSCOPY; IONIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; X RAY ANALYSIS;

BIPHASIC MEDIA; ISOLATED YIELD; LIGANDS; POLYDISPERSITY;

RUTHENIUM;

EID: 2942746791     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034335b     Document Type: Article

References (102)

1. (a) Joó, F. In Catalysis by Metal Complexes; James, B. R., van Leeuwen, P. W. N. M., Series Eds.; Kluwer Academic Publishers: Dordrecht, 2001; Vol. 23, Aqueous Organometallic Catalysis, p 300, and references therein
2. (b) Joó, F. Acc. Chem. Res. 2002, 35, 738-745.
3. (c) Joó, F.; Kovács, J.; Bényei, A. C.; Nadasdi, L.; Laurenczy, G. Chem. Eur. J. 2001, 7, 193-199.
4. (d) Laurenczy, G.; Joó, F.; Nadasdi, L. Inorg. Chem. 2000, 39, 5083-5088.
5. (e) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45.
6. (f) Joó, F.; Kovács, J.; Bényei, A. C.; Kathó, Á. Angew. Chem., Int. Ed. 1998, 37, 969-970.
7. (a) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, 1998; p 615, and references therein
8. (b) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
9. (a) Süss-Fink, G.; Faure, M.; Ward, T. R. Angew. Chem., Int. Ed. 2002, 41, 99-101.
10. (b) Cherioux, F.; Maisse-Francois, A.; Neels, A.; Stoeckli-Evans, H.; Süss-Fink, G. J. Chem. Soc., Dalton Trans. 2001, 14, 2184-2187.
11. (c) Süss-Fink, G.; Meister, G.; Haak, S.; Rheinwald, G.; Stoeckli-Evans, H. New J. Chem. 1997, 21, 785-790.
12. (d) Süss-Fink, G.; Meister, A.; Meister, G. Coord. Chem. Rev. 1995, 143, 97-111.
13. (a) Salignac, B.; Grundler, P. V.; Cayemittes, S.; Frey, U.; Scopelliti, R.; Merbach, A. E.; Hedinger, R.; Hegetschweiler, K.; Alberto, R.; Prinz, U.; Raabe, G.; Koelle, U.; Hall, S. Inorg. Chem. 2003, 42, 3516-3526.
14. (b) Koelle, U.; Goerissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911-917.
15. (c) Dadci, L.; Elias, H.; Frey, U.; Hoernig, A.; Koelle, U.; Merbach, A. E.; Paulus, H.; Schneider, J. S. Inorg. Chem. 1995, 34, 306-315.
16. (d) Koelle, U. Coord. Chem. Rev. 1994, 135/136, 623-650.
17. (e) Koelle, U. New J. Chem. 1992, 16, 157-169.
18. (f) Koelle, U.; Flunkert, G.; Goerissen, R.; Schmidt, M. U.; Englert, U. Angew. Chem., Int. Ed. Engl. 1992, 31, 440-442.
19. (g) Koelle, U.; Fuss, B. Chem. Ber. 1984, 117, 753-762.
20. (a) Ogo, S.; Uehara, K.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 3020-3021.
21. (b) Ogo, S.; Nakai, H.; Watanabe, Y. J. Am. Chem. Soc. 2002, 124, 597-601.
22. (c) Nakai, H.; Ogo, S.; Watanabe, Y. Organometallics 2002, 21, 1674-1678.
23. (d) Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903-4910.
24. Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199, and references therein.
25. Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.:, Thomson Science: London, 1998; p 310, and references therein.
26. (a) Mecking, S.; Held, A.; Bauers, F. M. Angew. Chem., Int. Ed. 2002, 41, 544-561, and references therein.
27. (b) Held, A.; Kudmila K.; Zuideveld, M. A.; Thomann, R.; Mecking, S.; Schmid, M.; Pietruschka, R.; Lindner, E.; Khanfar, M.; Sunjuk, M. Macromolecules 2002, 35, 3342-3347.
28. (c) Bauers, F. M.; Mecking, S. Angew. Chem., Int. Ed. 2001, 40, 3020-3022.
29. (d) Bauers, F. M.; Mecking, S. Macromolecules 2001, 34, 1165-1171.
30. (e) Held, A.; Mecking, S. Chem. Eur. J. 2000, 6, 4623-4629.
31. (f) Held, A.; Bauers, F. M.; Mecking, S. Chem. Commun. 2000, 301-302.
32. (a) Lynn, D. M.; Mohr, B.; Grubbs, R. H.; Henling, L. M.; Day, M. W. J. Am. Chem. Soc. 2000, 122, 6601-6609.
33. (b) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627-1628.
34. (c) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784-790.
35. (d) Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 7542-7543.
36. Manders, B.; Sciandrone, L.; Hauck, G.; Kristen, M. O. Angew. Chem., Int. Ed. 2001, 40, 4006-4007.
37. (a) Fuji, Y.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 2002, 35, 2949-2954.
38. (b) Sawamoto, M.; Kamigaito, M. Macromol. Symp. 2002, 177, 17-24.
39. (c) Sawamoto, M.; Kamigaito, M. Macromol. Symp. 2000, 161, 11-18.
40. (d) Nishikawa, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 1999, 32, 2204-2209.
41. (a) Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1203, and references therein.
42. (b) Wang, L.; Lu, R. S.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1993, 115, 6999-7000.
43. (a) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-315, and references therein
44. (b) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428-447, and references therein.
45. (a) Bielawski, C. W.; Benitez, D.; Grubbs, R. H. Science 2002, 297, 2041-2044.
46. (b) Younkin, T. R.; Connor, E. F.; Henderson, J. I.; Friedrich, S. K.; Grubbs, R. H.; Bansleben, D. A. Science 2000, 287, 460-462.
47. (a) Komon, Z. J. A.; Diamond, G. M.; Leclerc. M. K.; Murphy, V.; Okazaki, M.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 15280-15285.
48. (b) Lee, B. Y.; Bazan, G. C.; Vela. J.; Komon, Z. J. A.; Bu, X. J. Am. Chem. Soc. 2001, 123, 5352-5353.
49. (c) Komon, Z. J. A.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 12379-12380.
50. (d) Komon, Z. J. A.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 1830-1831.
51. (e) Rogers, J. S.; Bu, X.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 730-731.
52. (f) Putzer, M. A.; Rogers, J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 8112-8113.
53. Komiya, S.; Yamamoto, A.; Ikeda, S. Bull. Chem. Soc. Jpn. 1975, 48, 101-107.
54. (a) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3745, and references therein.
55. (b) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990, and references therein.
56. (a) Kamigaito, M.; Watanabe, Y.; Ando, T.; Sawamoto, M. J. Am. Chem. Soc. 2002, 124, 9994-9995.
57. (b) Watanabe, Y.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 2001, 34, 4370-4374.
58. (c) Takahashi, H.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 1999, 32, 3820-3823.
59. (a) Simal, F.; Demonceau, A.; Noels, A. F. Angew. Chem., Int. Ed. 1999, 38, 538-540.
60. (b) Delaude, L.; Delfosse, S.; Richel, A.; Demonceau, A.; Noels, A. F. Chem. Commun. 2003, 1526-1527.
61. (a) Desurmont, G.; Li, Y.; Yasuda, H.; Maruo, T.; Kanehisa, N.; Kai, Y. Organometallics 2000, 19, 1811-1813.
62. (b) Yasuda, H.; Yamamoto, H.; Yokota, K.; Miyake, S.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 4908-4910.
63. (c) Yasuda, H.; Furo, M.; Yamamoto, H. Macromolecules 1992, 25, 5115-5116.
64. (a) Capacchione, C.; Proto, A.; Ebeling, H.; Muelhaupt, Rolf, Moeller, K.; Spaniol, T. P.; Okuda, J. J. Am. Chem. Soc. 2003, 125, 4964-4965.
65. (b) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76.
66. (c) Braune, W.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 64-68.
67. (d) Hultzsch, K.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 1999, 38, 227-230.
68. (a) Chirik, P. J.; Zubris, D. L.; Ackerman, L. J.; Henling, L. M.; Day, M. W.; Bercaw, J. E. Organometallics 2003, 22, 172-187.
69. (b) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045-1053.
70. (c) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623-4640.
71. (d) Bazan, G. C.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1993, 12, 2126-2130.
72. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606-7607.
73. (f) Burger, B.; Thompson, M. K.; Cotter, W. D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566-1577.
74. (g) Shapiro, P. J.; Bunel, E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867-869.
75. (a) Casey, C. P.; Tunge, J. A.; Lee, T.-Y.; Carpenetti, D. W., II. Organometallics 2002, 21, 389-396.
76. (b) Casey, C. P.; Lee, T.-Y.; Tunge, J. A.; Carpenetti, D. W., II. J. Am. Chem. Soc. 2001, 123, 10762-10763.
77. (c) Casey, C. P.; Carpenetti, D. W., II; Sakurai, H. Organometallics 2001, 20, 4262-4265.
78. (d) Casey, C. P.; Klein, J. F.; Fagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320-4330.
79. (e) Casey, C. P.; Carpenetti, D. W., II; Sakurai, H. J. Am. Chem. Soc. 1999, 121, 9483-9484.
80. (a) Stern, D.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 9558-9575.
81. (b) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N. Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091-8103.
82. (c) Jeske, G.; Schock, L. E.; Mauermann, H.; Swepston, P. N. Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103-8110.
83. (d) Jeske, G.; Lauke, H.; Mauermann, H.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8111-8118.
84. (a) Hayashi, H.; Ogo, S.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 14266-14267.
85. (b) Ogo, S.; Abura, T.; Watanabe, Y. Organometallics 2002, 21, 2964-2969.
86. (c) Abura, T.; Ogo, S.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 4149-4154.
87. (a) Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832-2847, and references therein.
88. (b) Zhang, X.; Chen, P. Chem. Eur. J. 2003, 9, 1852-1859.
89. (c) Volland, M.; August, O.; Adlhart, C.; Kiener, C. A.; Chen, P.; Hofmann, P. Chem. Eur. J. 2001, 7, 4621-4632.
90. (d) Adlhart, C.; Hinderling, C.; Baumann, H.; Chen, P. J. Am. Chem. Soc. 2000, 122, 8204-8214.
91. (e) Hinderling, C.; Chen, P. Angew. Chem., Int. Ed. 1999, 38, 2253-2256.
92. (f) Hinderling, C.; Adlhart, C.; Chen, P. Angew. Chem., Int. Ed. 1998, 37, 2685-2689.
93. (g) Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126.
94. (h) Hinderling, C.; Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1997, 119, 10793-10804.
95. (i) Hinderling, C.; Plattner, D. A.; Chen, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 243-244.
96. Landis, C. R.; Rosaaen, K. A.; Sillars, D. R. J. Am. Chem. Soc. 2003, 125, 1710-1711.
97. (a) Glasoe, P. K.; Long, P. A. J. Phys. Chem. 1960, 64, 188-190.
98. (b) Mikkelsen, K.; Nielsen, S. O. J. Phys. Chem. 1960, 64, 632-637.
99. Smith, K.-T.; Rømming, C.; Tilset, M. J. Am. Chem. Soc. 1993, 115, 8681-8689.
100. Lindner, E.; Pautz, S.; Fawzi, R.; Steimann, M. Organomeallics 1998, 17, 3006-3014.
101. Nakamoto, K. In Infrared and Roman Spectra of Inorganic and Coordination Compounds, 5th ed.; Wiley: New York, 1997, and references therein.
102. Kawamura, T.; Toshima, N. Macromol. Rapid Commun. 1994, 15, 479-486.