Si-Si/Si-C/Si-O/Si-N coupling of hydrosilanes to useful silicon-containing materials

Synlett

Volumn , Issue 5, 2004, Pages 761-772

  Kim, Bo Hye ^a,b,c,d,e,f   Cho, Myong Shik ^a,b,g   Woo, Hee Gweon ^{a,b,c,d,e,f,h,i,j,k,l,m,n,o,p,q,r}  

^a Chonnam National University   (South Korea)

^b Chonnam National University ^*

^c HARVARD UNIVERSITY   (United States)

^d UNIVERSITY OF OXFORD   (United Kingdom)

^e UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^f Seonam University   (South Korea)

^g Seonam University   (South Korea)

^h Yonsei University   (South Korea)

ⁱ Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^j UNIVERSITY OF CALIFORNIA   (United States)

^k MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^l MCGILL UNIVERSITY   (Canada)

^m Chemistry Department   (South Korea)

ⁿ CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^o UNIVERSITY OF WISCONSIN MADISON   (United States)

^p UNIVERSITY OF NEW ORLEANS   (United States)

^q SORBONNE UNIVERSITÉ   (France)

^r UNIVERSITY OF TOKYO   (Japan)

more..

Author keywords

Consecutive hydrosilation; Dehydrocoupling; Hydrosilanes; Metallocene catalyst; Redistributive coupling

Indexed keywords

CARBON; HYDROGEN; NITROGEN; OXYGEN; SILANE; SILICON;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CLINICAL RESEARCH; COUPLING FACTOR; STRUCTURE ANALYSIS;

EID: 1942457239     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820016     Document Type: Article

References (112)

1. Zubay, G. Biochemistry; Addison-Wesley Publishing Company Inc.: Reading, 1983.
2. March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1985.
3. Odian, G. Principles of Polymerization, 3rd ed.; Wiley & Sons: New York, 1991.
4. (a) Inorganic and Organometallic Polymers II, ACS Symposium Series 572; Wisian-Neilson, P.; Allock, H. R.; Wynne, K. J., Eds.; EdS., American Chemical Society: Washington DC, 1994.
5. (b) Design Activation and Transformation of Organometallic into Common and Exotic Materials, NATO ASI Series E, No. 141; Laine, R. M., Ed.; Martinus Nijhof: Amsterdam, 1988.
6. Allock, H. R.; Lampe, F. W. Contemporary Polymer Chemistry, 2nd ed.; Prentice-Hall Inc.: New York, 1990, Chap. 9.
7. (a) Silicon-containing Polymers; Jones, R. G., Ed.; The Royal Society of Chemistry: Cambridge, 1995.
8. (b) Silicon in Polymer Synthesis; Kricheldorf, H. R., Ed.; Springer-Verlag: Berlin, 1996.
9. (a) Walsh, R. Acc. Chem. Res. 1981, 14, 246.
10. (b) Dewar, M. J. S. Organometallics 1986, 5, 375.
11. West, R. J. Organomet. Chem. 1986, 300, 327.
12. Silicon-based Polymer Science, Advances in Chemistry Series 224; Ziegler, J. M.; Fearson, F. W. G., Eds.; American Chemical Society: Washington DC, 1990.
13. Miller, R. D.; Michl, J. Chem. Rev. 1989, 89, 1359; and references cited therein.
14. Gauvin, F.; Harrod, J. F.; Woo, H.-G. Adv. Organomet. Chem. 1998, 42, 363; and references cited therein.
15. Tilley, T. D. Acc. Chem. Res. 1993, 26, 22; and references cited therein.
16. Corey, J. Y. Adv. Silicon Chem. 1991, 1, 327; and references cited therein.
17. Banovetz, J. P.; Stein, R. M.; Waymouth, R. M. Organometallics 1991, 10, 3430.
18. Choi, N.; Onozawa, S.-Y.; Sakakura, T.; Tanaka, M. Organometallics 1997, 16, 2765.
19. Dioumaev, V. K.; Harrod, J. F. Organometallics 1994, 13, 1548.
20. Li, H.; Gauvin, F.; Harrod, J. F. Organometallics 1993, 12, 575.
21. Dioumaev, V. K.; Harrod, J. F. Organometallics 1996, 15, 3859.
22. Campbell, W. H.; Hilty, T. K.; Yurga, L. Organometallics 1989, 8, 2615.
23. Tilley, T. D. Comments Inorg. Chem. 1990, 10, 37.
24. (a) Aiken, C.; Harrod, J. F.; Gill, U. S. Can. J. Chem. 1987, 65, 1804.
25. (b) Harrod, J. F.; Yun, S. S. Organometallics 1987, 6, 1381.
26. (c) Aitken, C.; Barry, J.-P.; Gauvin, F.; Harrod, J. F.; Malek, A.; Rousseau, D. Organometallics 1989, 8, 1732.
27. (d) Harrod, J. F.; Ziegler, T.; Tschinke, V. Organometallics 1993, 12, 2883.
28. (e) Britten, J.; Mu, Y.; Harrod, J. F.; Polowin, J.; Baird, M. C.; Samuel, E. Organometallics 1993, 12, 2672.
29. (a) Woo, H.-G.; Tilley, T. D. J. Am. Chem. Soc. 1989, 111, 3757.
30. (b) Woo, H.-G.; Tilley, T. D. J. Am. Chem. Soc. 1989, 111, 8043.
31. (c) Woo, H.-G.; Walzer, J. F.; Tilley, T. D. Macromolecules 1991, 24, 6863.
32. (d) Woo, H.-G.; Heyn, R. H.; Tilley, T. D. J. Am. Chem. Soc. 1992, 114, 5698.
33. (e) Woo, H.-G.; Walzer, J. F.; Tilley, T. D. J. Am. Chem. Soc. 1992, 114, 7047.
34. (f) Banovetz, J. P.; Suzuki, H.; Waymouth, R. M. Organometallics 1993, 12, 4700.
35. (g) Imori, T.; Woo, H.-G.; Walzer, J. F.; Tilley, T. D. Chem. Mater. 1993, 5, 1487.
36. (h) Corey, J. Y.; Huhmann, J. L.; Zhu, X.-H. Organometallics 1993, 12, 1121.
37. (a) Woo, H.-G.; Kim, S.-Y.; Han, M.-K.; Cho, E. J.; Jung, I. N. Organometallics 1995, 14, 2415.
38. (b) Woo, H.-G.; Song, S.-J. Chem. Lett. 1999, 457.
39. (c) Woo, H.-G.; Kim, S.-Y.; Kim, W.-G.; Cho, E. J.; Yeon, S. H.; Jung, I. N. Bull. Korean Chem. Soc. 1995, 16, 1109.
40. (d) Woo, H.-G.; Song, S. J.; Han, M. K.; Cho, E. J.; Jung, I. N. Bull. Korean Chem. Soc. 1995, 16, 1242.
41. (e) Woo, H.-G.; Song, S.-J. Bull. Korean Chem. Soc. 1996, 17, 494.
42. (f) Woo, H.-G.; Song, S. J. Bull. Korean Chem. Soc. 1996, 17, 1040.
43. (g) Woo, H.-G.; Kim, B.-H.; Song, S.-J.; Han, M.-K.; Kim, S.-Y.; Sung, A.-Y.; Kim, J. H.; Lee, J.-S. Bull. Korean Chem. Soc. 2000, 21, 935.
44. West, R. In Comprehensive Organometallic Chemistry II; Davis, A. G., Ed.; Pergamon Press: Oxford, 1995, 77-110.
45. Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhau, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740.
46. (a) Sohn, H.; Woo, H.-G.; Powell, D. R. Chem. Commun. 2000, 697.
47. (b) Woo, H.-G.; Kim, B.-H.; Sohn, H. Chem. Lett. 2000, 544.
48. Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974.
49. (a) Sohn, H.; Huddleston, R. R.; Powell, D. R.; West, R. J. Am. Chem. Soc. 1999, 121, 2935.
50. (b) Tamao, K.; Yamaguich, S. Pure Appl. Chem. 1996, 68, 139.
51. (c) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
52. (d) Yamaguchi, S.; Jin, R.-Z.; Tamao, K. J. Am. Chem. Soc. 1999, 121, 2937.
53. (e) Kanno, K.; Ichinobe, M.; Kabuto, C.; Kira, M. Chem. Lett. 1998, 99.
54. (a) Sanji, T.; Sakai, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1998, 120, 4552.
55. (b) West, R. personal communication
56. (c) Woo, H.-G.; Kim, B.-H.; Song, S.-J.; Sohn, H. unpublished results
57. Chauhan, B. P. S.; Shimizu, T.; Tanaka, M. Chem. Lett. 1997, 785.
58. Trogler, W. C.; Sohn, H.; Liu, S.; Toal, S. Abstracts of Papers, 225th ACS National Meeting; ACS: Washington D.C., 2003, INOR-746.
59. Kim, B.-H.; Woo, H.-G. Organometallics 2002, 21, 2796.
60. (a) Hong, J.-H.; Boudjouk, P. J. Am. Chem. Soc. 1993, 115, 5883.
61. (b) Hong, J.-H.; Boudjouk, P.; Castellino, S. Organometallics 1994, 13, 3387.
62. (c) West, R.; Sohn, H.; Bankwitz, U.; Calabrese, J.; Apeloig, Y.; Mueller, T. J. Am. Chem. Soc. 1995, 117, 11608.
63. (a) Lukevics, E.; Dzintara, M. J. Organomet. Chem. 1985, 295, 265.
64. (b) Pitt, C. G. Homoatomic Rings Chains and Macromolecules of Main-Group Elements; Rheingold, A. L., Ed.; Elsevier Scientific Publishing Company: Amsterdam, 1977, 203.
65. Bedard, T. C.; Corey, J. Y. J. Organomet. Chem. 1992, 428, 315.
66. (a) Sommer, L. H.; Lyons, J. E. J. Organomet. Chem. 1967, 89, 1521.
67. (b) Corriu, R. J. P.; Moreau, J. J. J. Chem. Soc., Chem. Commun. 1973, 38.
68. (c) Ojima, I.; Kogure, T.; Nihonyanagi, M.; Kono, H.; Inaba, S.; Nagai, Y. Chem. Lett. 1973, 501.
69. Kim, B.-H.; Park, S.-H.; Kim, M.-S.; Woo, H.-G., manuscript in preparation.
70. Kim, B.-H.; Cho, M.-S.; Kim, M.-A.; Woo, H.-G. J. Organomet. Chem. 2003, 685, 93.
71. Laine, R. M.; Babonneau, F. Chem. Mater. 1993, 5, 260.
72. Cho, M.-S.; Kim, B.-H.; Kong, J.-I.; Sung, A.-Y.; Woo, H.-G. J. Organomet. Chem. 2003, 685, 99.
73. Hong, L.-Y.; Cao, F.; Kim, D.-J.; Woo, H.-G.; Kim, B.-H.; Cho, M.-S.; Li, X.-D.; Kim, D.-P. J. Oranmomet. Chem. 2003, 687, 27.
74. (a) Kralicek, J.; Kubanek, V.; Kondelikova, J. German Patent 2:301,784, 1973.
75. (b) Kralicek, J.; Kubanek, V. Kondelikova J., Casensky B., Machacek J.; German Patent 2:445,647, 1976.
76. (c) Bukac, Z.; Sebenda, J. U.S. Patent 3:962,239, 1976.
77. (a) Becker, B.; Corriu, R. J. P.; Guerin, C.; Henner, B. J. L. J. Organomet. Chem. 1989, 369, 147.
78. (b) Becker, B.; Corriu, R.; Guerin, C.; Henner, B. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 409.
79. (c) Corriu, R. J. P. J. Organomet. Chem. 1990, 400, 81.
80. Riviere, P.; Satge, J.; Soula, D. J. Organomet. Chem. 1974, 72, 329.
81. Speier, J. L.; Zimmerman, R. E. J. Am. Chem. Soc. 1955, 77, 6395.
82. Woo, H.-G.; Song, S.-J.; Cho, E. J.; Jung, I. N. Bull. Korean Chem. Soc. 1995, 16, 1109.
83. Seyferth, D.; Lang, H. Organometallics 1991, 10, 551.
84. Armitage, A. D. In Comprehensive Organometallic Chemistry, Volume 2; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Peramon Press: Oxford, 1982, Chap. 1.
85. Woo, H.-G.; Song, S.-J.; You, H.; Cho, E. J.; Jung, I. N. Bull. Korean Chem. Soc. 1996, 17, 475.
86. Woo, H.-G.; Kim, S.-Y.; Kim, W.-G.; Yeon, S. H.; Cho, E. J.; Jung, I. N. Bull. Korean Chem. Soc. 1995, 16, 1109.
87. Woo, H.-G.; Kim, B.-H.; Cho, M.-S.; Hwang, T. S. Proceedings of International Symposium on Silicon-containing Polymers and Applications; Kanagawa: Japan, 2001, 49.
88. Speier, J. L. Adv. Organomet. Chem. 1978, 17, 407.
89. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987, 564.
90. Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
91. Seitz, F.; Wrighton, M. S. Angew. Chem. Int. Ed. 1989, 28, 762.
92. (a) Hao, L.; Harrod, J. F.; Lebuis, A.-M.; Mu, Y.; Shu, R.; Samuel, E.; Woo, H.-G. Angew. Chem. Int. Ed. 1998, 37, 3126.
93. (b) Harrod, J. F.; Shu, R.; Woo, H.-G.; Samuel, E. Can. J. Chem. 2001, 79, 1075.
94. (a) Hong, L.-Y.; Woo, H.-G.; Ham, H.-S. Bull. Korean Chem. Soc. 1995, 16, 360.
95. (b) Woo, H.-G.; Hong, L.-Y.; Kim, S.-Y.; Park, S.-H.; Song, S.-J.; Ham, H.-S. Bull. Korean Chem. Soc. 1995, 16, 774.
96. (c) Woo, H.-G.; Hong, L.-Y.; Yang, S.-Y.; Park, S.-H.; Song, S.-J.; Ham, H.-S. Bull. Korean Chem. Soc. 1995, 16, 1056.
97. (d) Woo, H.-G.; Hong, L.-Y.; Park, J.-Y.; Jeong, Y.-T.; Park, H.-R.; Ham, H.-S. Bull. Korean Chem. Soc. 1996, 17, 16.
98. (e) Woo, H.-G.; Park, S.-H.; Park, J.-Y.; Yang, S.-Y.; Ham, H.-S. Bull. Korean Chem. Soc. 1996, 17, 373.
99. (f) Woo, H.-G.; Park, S.-H.; Hong, L.-Y.; Kang, H.-G.; Song, S.-J.; Ham, H.-S. Bull. Korean Chem. Soc. 1996, 17, 376.
100. (g) Woo, H.-G.; Park, S.-H.; Hong, L.-Y.; Yang, S.-Y.; Kang, H.-G.; Ham, H.-S. Bull. Korean Chem. Soc. 1996, 17, 532.
101. (h) Woo, H.-G.; Park, J.-Y.; Hong, J.-Y.; Song, S.-J.; Ham, H.-S.; Kim, W.-G. Bull. Korean Chem. Soc. 1996, 17, 560.
102. (i) Woo, H.-G.; Oh, E.-M.; Park, J.-H.; Kim, B.-H.; Kim, Y.-N.; Yoon, C.-H.; Ham, H.-S. Bull. Korean Chem. Soc. 2000, 21, 291.
103. (j) Woo, H.-G.; Lee, M.-S.; Kim, Y.-J.; Kim, B.-H.; Kong, J.-I.; Sung, A.-Y. Proceedings of International Symposium on Silicon-containing Polymers and Applications; Kanakagwa: Japan, 2001, 81.
104. (k) Woo, H.-G.; Lee, M.-S.; Kim, Y.-J.; Kim, B.-H.; Kim, Y.-S.; Sung, A.-Y. Proceedings of International Symposium on Silicon-containing Polymers and Applications; Kanakagwa: Japan, 2001, 85.
105. (l) Woo, H.-G.; Kim, B.-H.; Cho, M.-S.; Kim, D.-Y.; Choi, Y.-S.; Kwak, Y.-C.; Ham, H.-S.; Kim, D.-P.; Hwang, T. S. Bull. Korean Chem. Soc. 2001, 22, 1337.
106. (a) Odian, G. Principles of Polymerization, 3rd ed.; Wiley: New York, 1991, 222-223.
107. (b) Mimura, S.; Naito, H.; Kanemitsu, Y.; Matsukawa, K.; Inoue, H. J. Organomet. Chem. 2000, 611, 40.
108. (c) Peinado, C.; Alonso, A.; Catalina, F.; Schnabel, W. J. Photochem. Photobiol., A.: Chem. 2001, 141, 85.
109. Norrish, R. G.; Simons, J. P. Proc. R. Soc. London, Ser. A 1959, 251, 4.
110. Chatgilialoglu, C.; Timokhin, V. I.; Zaborovskiy, A. B.; Lutsyk, D. S.; Prystansky, R. E. J. Chem. Soc., Perkin Trans. 2 2000, 577.
111. (a) Woo, H.-G.; Cho, M. S.; Lee, M.-S.; Kim, Y.-J. Proceedings of International Symposium on Silicon-containing Polymers and Applications; Kanagawa: Japan, 2001, 97.
112. (b) Woo, H.-G.; Lee, S.-E.; Kwak, Y.-C.; Kim, B.-H.; Ham, H.-S. Proceedings of International Symposium on Silicon-containing Polymers and Applications; Kanagawa: Japan, 2001, 69.