Palladium-catalyzed disilylation of o-quinodimethanes: Synthesis of 9- and 10-membered disilacarbocycles

Organic Letters

Volumn 10, Issue 19, 2008, Pages 4319-4322

  Yoshida, Hiroto ^a   Nakano, Saori ^a   Mukae, Masashi ^a   Ohshita, Joji ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349111971     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801788t     Document Type: Article

References (43)

1. For reviews, see: (a) Oppolzer, W. Synthesis 1978, 793.
2. (b) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873.
3. (c) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proc. Int. 1991, 23, 237.
4. (d) Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199.
5. (e) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 4.1, pp 385-396.
6. Nemoto, H.; Fukumoto, K. Tetrahedron 1998, 54, 5425.
7. (a) Kametani, T.; Fukumoto, K. Acc. Chem. Res. 1976, 9, 319.
8. (b) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
9. Morris, J. L.; Becker, C. L.; Fronczek, F. R.; Daly, W. H.; McLaughlin, M. L. J. Org. Chem. 1994, 59, 6484.
10. (a) Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
11. (b) Diederich, F.; Jonas, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2445.
12. (c) Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235.
13. (d) Belik, P.; Gügel, A.; Kraus, A.; Walter, M.; Müllen, K. J. Org. Chem. 1995, 60, 3307.
14. For polymerization of o-quinodimethanes, see: Chino, K.; Takata, T.; Endo, T. Macromolecules 1997, 30, 6715.
15. For o-quinodimethanes as nitric oxide cheletropic traps, see: Korth, H. G. In Free Radicals in Biology and Environment; Springer: New York, 1997; NATO ASI Series 3, Vol. 27, pp 331-349.
16. Yoshida, H.; Nakano, S.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Org. Lett. 2006, 8, 4157.
17. We have also reported catalytic insertion reactions of arynes into an element-element σ-bond. (a) Yoshida, H.; Honda, Y.; Shirakawa, E.; Hiyama, T. Chem. Commun. 2001, 1880.
18. (b) Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2003, 125, 6638.
19. (c) Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. Organometallics 2005, 24, 156.
20. (d) Ikadai, J.; Yoshida, H.; Ohshita, J.; Kunai, A. Chem. Lett. 2005, 34, 56.
21. (e) Yoshida, H.; Tanino, K.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed. 2004, 43, 5052.
22. (f) Yoshida, H.; Tanino, K.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 5678.
23. For reviews on catalytic insertion reactions of carbon-carbon multiple bonds into an element-element σ-bond, see: (a) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
24. (b) Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221.
25. (c) Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320.
26. For pioneering works on the fluoride ion-induced generation of o-quinodimethanes, see: (a) Ito, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 863.
27. (b) Ito, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 7609.
28. Diels-Alder reaction of o-quinodimethanes using 2-[(trimethylsilyl)methyl]benzyl acetate has been reported; see: (a) Askari, S.; Lee, S.; Perkins, R. R.; Scheffer, J. R. Can. J. Chem. 1985, 63, 3526.
29. (b) Kuwano, R.; Shige, T. Chem. Lett. 2005, 34, 728.
30. (a) Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1.
31. (b) Azarian, D.; Dua, S. S.; Eabornand, C.; Walton, D. R. M. J. Organomet. Chem. 1976, 117, C55.
32. (c) Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 409.
33. (d) Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1987, 28, 4715.
34. (e) Shirakawa, E.; Kurahashi, T.; Yoshida. H.; Hiyama, T. Chem. Commun. 2000, 1895.
35. For palladium-catalyzed cross-couplings of benzylic carbonates, see: (a) Kuwano, R.; Yokogi, M. Org. Lett. 2005, 7, 945.
36. (b) Kuwano, R.; Yu, J.-Y. Heterocycles 2007, 74, 233.
37. (c) Nakao, Y.; Ebata, S.; Chen, J.; Imanaka, H.; Hiyama, T. Chem. Lett. 2007, 36, 606.
38. (d) Ohsumi, M.; Kuwano, R. Chem. Lett. 2008, 37, 796.
39. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912.
40. Palladacycle 4 has been reported to be a key intermediate in palladium-catalyzed formal [4 + 2] cycloaddition of o-quinodimethanes with olefins. Kuwano, R.; Shige, T. J. Am. Chem. Soc. 2007, 129, 3802.
41. For palladium-catalyzed carbostannylation of alkynes or arynes, which proceeds through a palladacycle, see: (a) Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 4290.
42. (b) Yoshida, H.; Shirakawa, E.; Nakao, Y.; Honda, Y.; Hiyama, T. Bull. Chem. Soc. Jpn. 2001, 74, 637.
43. (c) Matsubara, T. Organometallics 2003, 22, 4297.