General silaindene synthesis based on intramolecular reductive cyclization toward new fluorescent silicon-containing π-electron materials

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3707-3710

  Xu, Caihong ^a   Wakamiya, Atsushi ^b   Yamaguchi, Shigehiro ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; SILICON DERIVATIVE;

ARTICLE; CYCLIZATION; FLUORESCENCE; METHODOLOGY; MOLECULAR DYNAMICS; REDUCTION; SYNTHESIS;

EID: 7044263189     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0486932     Document Type: Article

References (36)

1. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
2. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
3. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
4. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
5. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
6. For recent indole preparations, see for instance: (a) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409. (b) Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764-4771. (c) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843-3846. (d) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277-1280. (e) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1587, (f) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488-2490 and references therein.
7. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
8. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
9. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
10. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
11. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
12. For recent benzo[b]furan preparations, see for instance: (a) Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518-527. (b) Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380. (c) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. (d) Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4, 4727-4729. (e) Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1. 2000, 4339-4346. (f) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Moro, L. Eur. J. Org. Chem. 1999, 1137-1141 and references therein.
13. For recent benzo[b]thiophene preparations, see for instance: (a) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380. (b) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651-654. (c) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011-6013 and references therein, (d) Kitamura, T.; Takachi, T.; Miyaji, M.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1994, 1907-1911.
14. For recent benzo[b]thiophene preparations, see for instance: (a) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380. (b) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651-654. (c) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011-6013 and references therein, (d) Kitamura, T.; Takachi, T.; Miyaji, M.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1994, 1907-1911.
15. For recent benzo[b]thiophene preparations, see for instance: (a) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380. (b) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651-654. (c) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011-6013 and references therein, (d) Kitamura, T.; Takachi, T.; Miyaji, M.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1994, 1907-1911.
16. For recent benzo[b]thiophene preparations, see for instance: (a) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377-4380. (b) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651-654. (c) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011-6013 and references therein, (d) Kitamura, T.; Takachi, T.; Miyaji, M.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1994, 1907-1911.
17. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
18. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
19. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
20. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
21. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
22. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
23. Conventional silaindene synthesis based on the reaction of dilithiostyrenes with halosilanes: (a) Korneev, S. M.; Kaufmann, D. E. Synthesis 2002, 491-496. (b) Ura, Y.; Li, Y.; Tsai, F.-Y.; Nakajima, K.; Kotora, M.; Takahashi, T. Heterocycles 2000, 52, 1171-1189. (c) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099-4102. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814-5815. (e) Rausch, M. D.; Klemann, L. P. J. Am. Chem. Soc. 1967, 89, 5732-5733. For other silaindene synthesis, see: (f) Kunai, A.; Yuzuriha, Y.; Naka, A.; Ishikawa, M. J. Organomet. Chem. 1993, 455, 77-81. (g) Barton, T. J.; Groh, B. L. Organometallics 1985, 4, 575-580.
24. Versatile synthesis of heteroindenes by the reaction of dilithiostyrenes with metal halides: Kurita, J.; Ishii, M.; Yasuike, S.; Tsuchiya, T. J. Chem. Soc., Chem. Commun. 1993, 1309-1310.
25. Märkl, G.; Berr, K.-P. Tetrahedron Lett. 1992, 33, 1601-1604.
26. Sudo. T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2000, 65, 8919-8923.
27. For silicon-containing π-electron compounds applicable to organic LEDs, see for instance: (a) Yamaguchi, S.; Tamao, K. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; pp 641-694 and references therein. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975. (c) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189-191. (d) Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. J. Organomet. Chem. 2002, 642, 137. (e) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740-1741.
28. For silicon-containing π-electron compounds applicable to organic LEDs, see for instance: (a) Yamaguchi, S.; Tamao, K. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; pp 641-694 and references therein. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975. (c) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189-191. (d) Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. J. Organomet. Chem. 2002, 642, 137. (e) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740-1741.
29. For silicon-containing π-electron compounds applicable to organic LEDs, see for instance: (a) Yamaguchi, S.; Tamao, K. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; pp 641-694 and references therein. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975. (c) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189-191. (d) Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. J. Organomet. Chem. 2002, 642, 137. (e) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740-1741.
30. For silicon-containing π-electron compounds applicable to organic LEDs, see for instance: (a) Yamaguchi, S.; Tamao, K. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; pp 641-694 and references therein. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975. (c) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189-191. (d) Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. J. Organomet. Chem. 2002, 642, 137. (e) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740-1741.
31. For silicon-containing π-electron compounds applicable to organic LEDs, see for instance: (a) Yamaguchi, S.; Tamao, K. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; pp 641-694 and references therein. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975. (c) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189-191. (d) Ohshita, J.; Kai, H.; Sumida, T.; Kunai, A.; Adachi, A.; Sakamaki, K.; Okita, K. J. Organomet. Chem. 2002, 642, 137. (e) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740-1741.
32. Use of silaindene-based materials for organic LEDs has been reported in a patent; see: Kohama, T.; Tominaga, T.; Murase, S. JP2002198176.
33. Yamaguchi, S.; Xu, C.; Tamao, K. J. Am. Chem. Soc. 2003, 125, 13662-13663.
34. Besides the diphenylacetylene derivative 1, we found that (trimethylsilyl)(o-dimethylsilylphenyl)acetylene also underwent the present reductive cyclization to give the corresponding cyclized product in a good yield.
35. 2 = 0.1533 for 2622 observed reflections with I > 2σ(I).
36. Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 7787.