Synthesis of alkenylsilanes via palladium(0)-catalyzed silylation of alkenyl iodides with hydrosilane

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9255-9257

  Murata, Miki ^a   Watanabe, Shinji ^a   Masuda, Yuzuru ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenyl halides; Alkenylsilane; Coupling reactions; Hydrosilane; Palladium catalyst

Indexed keywords

HALIDE; IODIDE; PALLADIUM COMPLEX; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CROSS LINKING; SYNTHESIS;

EID: 0033601463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01793-1     Document Type: Article

References (13)

1. For a recent review, see: Colvin, E. W. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 11, p. 313.
2. For recent reviews, see: (a) Ojima, I. In The Chemistry of Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1989; p. 1479.
3. (b) Takeda, T. In Synthesis of Organometallic Compounds; Komiya, S., Ed.; Wiley: New York, 1997; p. 391.
4. (a) Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1987, 28, 4715.
5. (b) Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem., Int. Ed. Engl. 1978, 17, 279.
6. Murata, M.; Suzuki, K.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 8569.
7. Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458.
8. It is known that the tertiary amine can act as a hydride source in the presence of palladium complex. See: (a) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429.
9. (b) Hagiwara, H.; Eda, Y.; Morohashi, K.; Suzuki, T.; Ando, M; Ito, N. Tetrahedron Lett. 1998, 39, 4055.
10. Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M.; Yamamoto, Y. Organometallics 1994, 13, 3233.
11. 3SiH 1c was not suitable as a silylating reagent.
12. Boukherroub, R.; Chatgilialoglu, C.; Manuel, G. Organometallics 1996, 15, 1508.
13. Unfortunately, in the case where (Z)-β-iodostyrene was used, the inversion of starting geometry occurred to give (E)-3a (35%) along with 4a (4%) and 5a (51%).