Stereodivergent Syntheses of (Z)- and (E)-Alkenylsilanes via Hydrosilylation of Terminal Alkynes Catalyzed by Rhodium(I) Iodide Complexes and Application to Silicon-Containing Polymer Syntheses

Organometallics

Volumn 23, Issue 8, 2004, Pages 1755-1765

  Mori, Atsunori ^a   Takahisa, Eisuke ^a   Yamamura, Yuichi ^a   Kato, Tsuyoshi ^a   Mudalige, Anoma P ^a   Kajiro, Hiroshi ^a   Hirabayashi, Kazunori ^a   Nishihara, Yasushi ^a   Hiyama, Tamejiro ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CATALYSIS; CATALYSTS; EMISSION SPECTROSCOPY; ISOMERS; PALLADIUM; POLYMERIZATION; POLYMERS; RHODIUM; SILICON; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

HYDROSILYLATION; POLYMER SYNTHESES; REGIOISOMERS;

ORGANOMETALLICS;

EID: 2342444385     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049922r     Document Type: Article

References (82)

1. (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1479-1526.
2. (b) Hiyama T.; Kusumoto T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8 pp 763-792
3. (a) Chandra, G.; Lo, P. Y.; Hitchcock, P. B. Lappert, M. F. Organometallics 1987, 6, 191-192.
4. (b) Iovel, I. G.; Goldberg, Y. S.; Shymanska, M.; Lukevics, E. Organometallics 1987, 6, 1410-1418.
5. (c) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 1943-1952.
6. The use of silanes with alkoxy or alkyl substituants resulted in the mixture of α- and β-E-adducts (ca. 30:70): (a) Sato, H.; Mizuno, K.; Mori, A.; Hiyama, T. Unpublished results: 70th Annual Meeting of Chemical Society of Japan, Tokyo, 1996 (3PB096). (b) Shintani, K., Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1909, 37, 705-710.
7. The use of silanes with alkoxy or alkyl substituants resulted in the mixture of α- and β-E-adducts (ca. 30:70): (a) Sato, H.; Mizuno, K.; Mori, A.; Hiyama, T. Unpublished results: 70th Annual Meeting of Chemical Society of Japan, Tokyo, 1996 (3PB096). (b) Shintani, K., Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1909, 37, 705-710.
8. (a) Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127-3133
9. (b) Faller, J. W.; Alliessi, D. G. Organometallics 2002, 21, 1743-1746, and references therein. Hydrosilylation of alkynes with other metal catalysts
10. (c) Doyle, M. P.; High, K. G.; Nesloney, C. L.; Clayton, T. W., Jr.; Lin, J. Organometallics 1990, 10, 1225-1226.
11. (d) Esteruelas, M. A.; Herrero, J.; Oro, L. A. Organometallics 1993, 12, 2377-2379
12. (e) Tanke, R. S.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984-7989.
13. (e) Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887-1889.
14. (f) Kawanami, Y.; Sonoda, Y.; Mori, T.; Yamamoto, K. Org. Lett. 2002, 4, 2825-2827.
15. (g) Chung, L. W.; Wu, Y.-D.; Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2003, 125, 11578-11582.
16. (h) Katayama, H.; Taniguchi, K.; Kobayashi, M.; Sagawa, T.; Minami, T.; Ozawa, F. J. Organomet. Chem. 2002, 645, 192-200.
17. (i) Crabtree, R. H. New J. Chem. 2003, 771-772.
18. Takeuchi, R.; Nitta, S.; Watanabe, D. J. Org. Chem. 1995, 60, 3045-3051.
19. Tamao, K.; Yoshida, J.; Takahashi, M.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Kurita, A.; Kumada, M. J. Am. Chem. Soc. 1978, 100, 290-292.
20. (a) Koike, T.; Du, X.; Sanada, T.; Danda, Y.; Mori, A. Angew. Chem., Int. Ed. 2003, 42, 89-91.
21. (b) Koike, T.; Mori, A. Synlett 2003, 1850-1852.
22. (c) Koike, T.; Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301-303.
23. (d) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 298-300.
24. (e) Fujii, T.; Koike, T.; Mori, A.; Osakada, K. Synlett 2002, 295-297.
25. (f) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774-10775.
26. (g) Mori, A.; Suguro, M. Synlett 2001, 845-847.
27. (h) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342-5349.
28. (i) Hirabayashi, K.; Ando, J.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409-1417.
29. (j) Mori, A.; Toriyama, T.; Kajiro, T.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550.
30. (a) Gamier, F. Angew. Chem., Int. Ed. Engl. 1989 28, 513-517.
31. (b) Yamamoto, T. Prog. Polym. Sci. 1992 17, 1153-1205.
32. Friend, R. H.; Gymer, E. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santas, D. A.; Bredas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 307, 121-127.
33. (a) Corriu, R. J. P.; Guerin, C.; Henner, B.; Kuhlmann, T.; Jean, A.; Garniner, F.; Yassar, J. Chem. Mater. 1990, 2, 351-352.
34. (b) Hua, C.-H.; West, R. Appl. Organomet. Chem. 1994, 8, 423-430.
35. (c) Ohshita, J.; Kanaya, D.; Ishikawa, M.; Koike, T.; Yamanaka, T. Macromolecules 1991, 24, 2106-2107.
36. (d) Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1990, 23, 4485-4486.
37. (e) Fang, M.-C.; Watanabe, A.; Matsuda, M. Chem. Lett. 1994, 13.
38. (f) Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X.; Garnier, F.; Yassar, A. J. Organomet. Chem. 1991, 417, C50-52.
39. (g) van Walree, C. A.; Roest, M. R.; Schuddeboom W.; Jenneskeiis, L. W.; Verhoeven, J. W.; Warman, J. M.; Kooijman, H.; Spek, A. L. J. Am. Chem. Soc. 1996, 118, 8395-8407.
40. (h) Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1995, 117, 5365-5366.
41. (i) bhikawa, M.; Hasegawa, Y.; Kunai, A. J. Organomet. Chem. 1990, 381, C57-59.
42. (j) Kim, H. K.; Ryu, M.-K.; Lee, S.-M. Macromolecules 1997, 30, 1236-1239.
43. (k) Brouwer, J. H.; Krasnikov, V. V.; Hilberer, A.; Hadziioannou, G. Adv. Mater. 1996, 8, 935-937.
44. (l) Itoh, M.; Mitsuzuka, M.; Iwata, K.; Inoue, K. Macromolecules 1994, 27, 7917-7919.
45. (m) Majchrzak, M.; Itami, Y.; Marciniec, B.; Pawluc, P. Tetrahedron Lett. 2000, 41, 10303-10307.
46. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
47. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
48. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
49. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
50. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
51. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
52. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
53. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
54. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
55. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
56. Polyaddition via hydrosilylation: (a) Chen, R. M.; Chien, K.-M.; Wong, K.-T.; Jin, B.-Y.; Luh, T.-Y.; Hou, J.-H.; Fann, W. J. Am. Chem. Soc. 1997, 119, 11321-11822. (b) Kunai, A.; Toyoda, E.; Nagamoto, I.; Horio, T.; Ishikawa, M. Organometallics 1996, 15, 75-83. (c) Pang, Y.; Ijadi-Maghsoodi, S.; Barton, T. J. Macromolecules 1993, 26, 5671-5675. (d) Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett. 1996, 517-518. (e) Shintani, K.; Ooi, O.; Mori, A.; Kawakami, Y. Polym. Bull. (Berlin) 1997, 38, 1-5. (f) Li, Y.; Kawakami, Y. Macromolecules 1998, 31, 5592-5597. (g) Itsuno, S.; Chao, D.; Ito, K. J. Polym. Sci. Part A 1993, 31, 287-291. (h) Tsumura, M.; Iwahara, T.; Hirose, T. Polym. J. 1995, 10, 1048-1053. (i) Dvornic, P.; Gerov, V. V.; Govedarica, M. N. Macromolecules 1994, 27, 7575-7580. (j) Kwak, G.; Masuda, T. Macromol. Rapid Commun. 2001, 22, 1233-1236. (k) Wang, F.; Kaafarani, B. R.; Neckers, D. C. Macromolecules 2003, 36, 8225-8230.
57. Preliminary communications: (a) Mori, A.; Takahisa, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443-444. (b) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Macromolecules 2000, 33, 1115-1116. See also: (c) Mori, A.; Takahisa, E.; Nishihara, Y.; Hiyama, T. Can. J. Chem. 2001, 79, 1522-1524. (d) Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825-831.
58. Preliminary communications: (a) Mori, A.; Takahisa, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443-444. (b) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Macromolecules 2000, 33, 1115-1116. See also: (c) Mori, A.; Takahisa, E.; Nishihara, Y.; Hiyama, T. Can. J. Chem. 2001, 79, 1522-1524. (d) Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825-831.
59. Preliminary communications: (a) Mori, A.; Takahisa, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443-444. (b) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Macromolecules 2000, 33, 1115-1116. See also: (c) Mori, A.; Takahisa, E.; Nishihara, Y.; Hiyama, T. Can. J. Chem. 2001, 79, 1522-1524. (d) Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825-831.
60. Preliminary communications: (a) Mori, A.; Takahisa, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443-444. (b) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Macromolecules 2000, 33, 1115-1116. See also: (c) Mori, A.; Takahisa, E.; Nishihara, Y.; Hiyama, T. Can. J. Chem. 2001, 79, 1522-1524. (d) Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825-831.
61. A part of the results was presented in OMCOS X (International Conference on Organometallic Chemistry Directed Towards Organic Synthesis) in Versailles, 1999: Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Polyhedron 2000, 19, 567-568.
62. (a) Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464.
63. (b) Hirabayashi, K.; Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2409-2415.
64. Young, J. F.; Osborn, J. A.; Jardine, F. H.; Wilkinaon, G. J. Chem. Soc., Chem. Commun. 1965, 131.
65. Hartley, F. R.; Murray, S. G.; Potter, D. M. J. Organomet. Chem. 1983, 254, 119-126.
66. The reactions of aryl-substituted alkynes such as phenylethyne cause undesirable polymerization to give polyalkynes: (a) Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105-1107. (b) Kishimoto, Y.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromoleculea 1996, 29, 5054-5055. (c) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209-1210.
67. The reactions of aryl-substituted alkynes such as phenylethyne cause undesirable polymerization to give polyalkynes: (a) Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105-1107. (b) Kishimoto, Y.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromoleculea 1996, 29, 5054-5055. (c) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209-1210.
68. The reactions of aryl-substituted alkynes such as phenylethyne cause undesirable polymerization to give polyalkynes: (a) Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105-1107. (b) Kishimoto, Y.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromoleculea 1996, 29, 5054-5055. (c) Goldberg, Y.; Alper, H. J. Chem. Soc., Chem. Commun. 1994, 1209-1210.
69. 2 also caused polymerization.
70. For reviews: (a) Hatanaka Y.; Hiyama, T. Pure Appl. Chem. 1984, 66, 1471-1478. (b) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10, pp 421-453.
71. For reviews: (a) Hatanaka Y.; Hiyama, T. Pure Appl. Chem. 1984, 66, 1471-1478. (b) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10, pp 421-453.
72. (a) Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 6051-6054.
73. (b) Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138-139.
74. (a) Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 566-568.
75. (b) Denmark, S. E.; Wang, Z. Org. Lett. 2001, 3, 1073-1076.
76. Although the monomers 30 and 31 were potentially a mixture of diastereomers, these were hardly separated and distinguished by NMR analyses in both monomers and polymers.
77. Conjugation through boron: Matsumi, N.; Naka, K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 10776-70777.
78. (a) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-629.
79. (b) Taylor, E. C.; Ray, P. S. J. Org. Chem. 1988, 53, 35-38.
80. Valerino, L. J. Chem. Soc. A 1957, 1711-1732.
81. Marciniec, B.; Walczuk-Gusciora, E.; Pietraszuk, C. Catal. Lett. 1998, 55, 125-127.
82. Zhang, R.; Pinhas, A. R.; Mark, J. E. Macromolecules 1997, 30, 2513-2515.