Rhodium-catalyzed synthesis of silafluorene derivatives via cleavage of silicon-hydrogen and carbon-hydrogen bonds

Journal of the American Chemical Society

Volumn 132, Issue 41, 2010, Pages 14324-14326

  Ureshino, Tomonari ^a   Yoshida, Takuya ^a   Kuninobu, Yoichiro ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON-HYDROGEN BOND; CH-BOND ACTIVATION; P-TERPHENYL; RHODIUM-CATALYZED SYNTHESIS; SIDE PRODUCTS;

CATALYSIS; HYDROGEN; RHODIUM; SYNTHESIS (CHEMICAL);

HYDROGEN BONDS;

CARBON; FLUORENE DERIVATIVE; HYDROGEN; RHODIUM; SILAFLUORENE DERIVATIVE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; DEHYDROGENATION;

EID: 77958052607     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107698p     Document Type: Article

References (48)

1. Chen, R.-F., Fan, Q.-L., Liu, S.-J., Zhu, R., Pu, K.-Y., and Huang, W. Synth. Met. 2006, 156, 1161
2. Mouri, K., Wakamiya, A., Yamada, H., Kajiwara, T., and Yamaguchi, S. Org. Lett. 2007, 9, 93
3. Sanchez, J. C., DiPasquale, A. G., Rheingold, A. L., and Trogler, W. C. Chem. Mater. 2007, 19, 6459
4. Sanchez, J. C. and Trogler, W. C. J. Mater. Chem. 2008, 18, 3143
5. Wang, E., Li, C., Zhuang, W., Peng, J., and Cao, Y. J. Mater. Chem. 2008, 18, 797
6. Mo, Y.-Q., Deng, X.-Y., Jiang, X., and Cui, Q.-H. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 3286
7. For stoichiometric synthesis of silafluorenes, see
8. Yamaguchi, S., Xu, C., and Tamao, K. J. Am. Chem. Soc. 2003, 125, 13662
9. Wang, Z., Fang, H., and Xi, Z. Tetrahedron Lett. 2005, 46, 499
10. Xu, C., Wakamiya, A., and Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638
11. Furukawa, S., Kobayashi, J., and Kawashima, T. J. Am. Chem. Soc. 2009, 131, 14192
12. Matsuda, T., Kadowaki, S., Goya, T., and Murakami, M. Org. Lett. 2007, 9, 133
13. Shimizu, M., Mochida, K., and Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 9760
14. Tobisu, M., Onoe, M., Kita, Y., and Chatani, N. J. Am. Chem. Soc. 2009, 131, 7506
15. Yabusaki, Y., Ohshima, N., Kondo, H., Kusamoto, T., Yamanoi, Y., and Nishihara, H. Chem.-Eur. J. 2010, 16, 5581
16. 2O.
17. 3, 58%; 1,2-bis(diphenylphosphino)ethane (dppe), trace; 1,3-bis(diphenylphosphino)propane (dppp), 52%; 1,4-bis(diphenylphosphino)butane (dppb), 45%; (R)-BINAP, 87%.
18. There have been some reports on rhodium-catalyzed transformations via C-H bond activation. See
19. Sakakura, T., Sodeyama, T., Sasaki, K., Wada, K., and Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221
20. Lim, Y.-G., Kang, J.-B., and Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201
21. Fujii, N., Kakiuchi, F., Yamada, A., Chatani, N., and Murai, S. Chem. Lett. 1997, 425
22. Lenges, C. P. and Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616
23. Jun, C.-H., Lee, D.-Y., Lee, H., and Hong, J.-B. Angew. Chem., Int. Ed. 2000, 39, 3070
24. Chatani, N., Asaumi, T., Ikeda, T., Yorimitsu, S., Ishii, Y., Kakiuchi, F., and Murai, S. J. Am. Chem. Soc. 2000, 122, 12882
25. Thalji, R. K., Ahrendt, K. A., Bergman, R. G., and Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692
26. Tanaka, K. and Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492
27. There have been several reports on transition-metal-catalyzed dehydrogenative silylation of aromatic compounds. See
28. Sakakura, T., Tokunaga, Y., Sodeyama, T., and Tanaka, M. Chem. Lett. 1987, 2375
29. Uchimaru, Y., El Sayed, A. M. M., and Tanaka, M. Organometallics 1993, 12, 2065
30. Kakiuchi, F., Igi, K., Matsumoto, M., Chatani, N., and Murai, S. Chem. Lett. 2001, 422
31. Tsukada, N. and Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 5022
32. We have recently reported on a transformation via C-H bond activation using a rhenium catalyst. See
33. Kuninobu, Y., Kawata, A., and Takai, K. J. Am. Chem. Soc. 2005, 127, 13498
34. Kuninobu, Y., Tokunaga, Y., Kawata, A., and Takai, K. J. Am. Chem. Soc. 2006, 128, 202
35. Kuninobu, Y., Nishina, Y., Shouho, M., and Takai, K. Angew. Chem., Int. Ed. 2006, 45, 2766
36. Kuninobu, Y., Nishina, Y., Nakagawa, C., and Takai, K. J. Am. Chem. Soc. 2006, 128, 12376
37. Kuninobu, Y., Nishina, Y., Okaguchi, K., Shouho, M., and Takai, K. Bull. Chem. Soc. Jpn. 2008, 81, 1393
38. Kuninobu, Y., Fujii, Y., Matsuki, T., Nishina, Y., and Takai, K. Org. Lett. 2009, 11, 2711
39. There have been several reports on rhodium-catalyzed dechlorination of chlorobenzene derivatives by hydrosilanes. For example, see: Esteruelas, M. A., Herrero, J., López, F. M., Martín, M., and Oro, L. A. Organometallics 1999, 18, 1110
40. 3, 5.0 mol%; 24 h). The silafluorene β could not be separated from γ by silica gel column chromatography or GPC.
41. Although the corresponding silafluorene was formed using biphenylhydrosilanes bearing two isopropyl groups on the silicon atom, the yield was only 12% (3,3-dimethyl-1-butene: 5.0 equiv, 180 °C, 24 h; not shown).
42. A purple fluorescence was observed when irradiating 254 nm UV light on a hexane solution of 2k or solid sample of 2k.
43. 3. Intermolecular hydrosilylation did not occur, and only silafluorene 2a was obtained in 93% yield. This result shows that only the formation of silafluorenes occurred even in the presence of styrene, which is an excellent substrate for hydrosilylation.
44. There has been a report on the formation of a H-Rh-Si species by oxidative addition of hydrosilanes to the rhodium center. See: Osakada, K., Koizumi, T.-a., and Yamamoto, T. Organometallics 1997, 16, 2063
45. There has been a report on a reaction via the formation of a rhodium(V) intermediate by oxidative addition of a C(aryl)-H bond to a silyl-rhodium intermediate. See: Ezbiansky, K., Djurovich, P. I., LaForest, M., Sinning, D. J., Zayes, R., and Berry, D. H. Organometallics 1998, 17, 1455
46. There have been a few examples of the synthesis of ladder-type bis-silicon-bridged p -terphenyls. See: Li, L., Xiang, J., and Xu, C. Org. Lett. 2007, 9, 4877
47. See also: ref 3.
48. A purple fluorescence was observed when irradiating 254 nm UV light on a hexane solution of 4 or solid sample of 4. See ref 19.