First examples of hypervalent enhancement of photoallylation by allylsilicon compounds via photoinduced electron transfer

Tetrahedron Letters

Volumn 46, Issue 31, 2005, Pages 5149-5151

  Nishigaichi, Yutaka ^a   Suzuki, Akira ^a   Saito, Takahiro ^a   Takuwa, Akio ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

Allylsilicon; Electron transfer; Hypervalency; Photoallylation

Indexed keywords

SILICON DERIVATIVE;

ALLYLATION; ARTICLE; ATOM; ELECTRON TRANSPORT; LIGHT;

EID: 21344449286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.124     Document Type: Article

References (22)

1. Y. Yamamoto, and N. Asao Chem. Rev. 93 1993 2207
2. In the photoreaction of aromatic ketones such as benzophenone and benzil, allyltrimethysilicon acts as a usual alkene to undergo [2+2] cycloaddition (oxetane formation) and hydrogen abstraction. A. Takuwa, H. Tagawa, H. Iwamoto, O. Soga, and K. Maruyama Chem. Lett. 1987 1091
3. A. Takuwa, Y. Nishigaichi, K. Yamashita, and H. Iwamoto Chem. Lett. 1990 639
4. A. Takuwa, Y. Nishigaichi, K. Yamashita, and H. Iwamoto Chem. Lett. 1990 1761
5. A. Takuwa, Y. Nishigaichi, and H. Iwamoto Chem. Lett. 1991 1013
6. A. Takuwa, Y. Nishigaichi, T. Yamaoka, and K. Iihama J. Chem. Soc., Chem. Commun. 1991 1359
7. A. Takuwa, J. Shiigi, and Y. Nishigaichi Tetrahedron Lett. 34 1993 3457
8. Y. Nishigaichi, N. Yoshida, M. Matsuura, and A. Takuwa Chem. Lett. 1999 803
9. K. Ohga, U.C. Yoon, and P.S. Mariano J. Org. Chem. 49 1984 213
10. S. Fukuzumi, M. Fujita, S. Noura, K. Ohkubo, T. Suenobu, Y. Araki, and O. Ito J. Phys. Chem. A 105 2001 1857
11. M. Mella, E. Fasani, and A. Albini J. Org. Chem. 57 1992 6210
12. K. Nakanishi, K. Mizuno, and Y. Otsuji Bull. Chem. Soc. Jpn. 66 1993 2371
13. Y. Kubo, T. Imaoka, T. Shiragami, and T. Araki Chem. Lett. 1986 1749
14. Photoallylation of an aromatic aldehyde with 3 was promoted by magnesium ion. S. Fukuzumi, T. Okamoto, and J. Otera J. Am. Chem. Soc. 116 1994 5503
15. Thermal reaction of hypervalent allylic silicon reagents: G. Cerveau, C. Chuit, R.J.P. Corriu, and C. Reye J. Organomet. Chem. 328 1987 C17
16. M. Kira, K. Sato, and H. Sakurai J. Am. Chem. Soc. 110 1988 4599
17. H. Sakurai Synlett 1989 1
18. A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga J. Org. Chem. 55 1990 2415
19. A. Hosomi, A. Shirahata, and H. Sakurai Tetrahedron Lett. 1978 3043
20. For the reactions with 7 and 8, it was confirmed that no reaction proceeded in the dark.
21. D. Rehm, and A. Weller Isr. J. Chem. 8 1970 259
22. K.P. Dockery, J.P. Dinnocenzo, S. Farid, J.L. Goodman, I.R. Gould, and W.P. Todd J. Am. Chem. Soc. 119 1997 1876