A Novel Reduction of Zinc(II) Chloride with Samarium Metal and its Application to Silylation of 1-Alkynes

Synlett

Volumn 1996, Issue 7, 1996, Pages 637-639

  Sugita, Hikaru ^a   Hatanaka, Yasuo ^c   Hiyama, Tamejiro ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041863613     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5582     Document Type: Article

References (33)

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20. 2 has been successfully utilized for the palladium-catalyzed reactions as a reducing agent. (a) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 601. (b) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron, Lett. 1986, 27, 5237. (c) Tabuchi, T. Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (e) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2275. (f) Mikami, K.; Yoshida, A.; Matsumoto, S.; Feng, F.; Matsumoto, Y.; Sugino, A.; Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1995, 36, 907.
21. 2 has been successfully utilized for the palladium-catalyzed reactions as a reducing agent. (a) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 601. (b) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron, Lett. 1986, 27, 5237. (c) Tabuchi, T. Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (d) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (e) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2275. (f) Mikami, K.; Yoshida, A.; Matsumoto, S.; Feng, F.; Matsumoto, Y.; Sugino, A.; Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1995, 36, 907.
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24. 2 and used independently for various reactions. (a) Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. (b) Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Lett. 1994, 379. (c) Murakami, M.; Hayashi, M.; Ito, Y. Synlett. 1994, 179. (d) Matsubara, S.; Horiuchi, M.; Takai, K.; Utimoto, K. Chem. Lett. 1995, 259.
25. 2 and used independently for various reactions. (a) Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. (b) Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Lett. 1994, 379. (c) Murakami, M.; Hayashi, M.; Ito, Y. Synlett. 1994, 179. (d) Matsubara, S.; Horiuchi, M.; Takai, K.; Utimoto, K. Chem. Lett. 1995, 259.
26. 2 and used independently for various reactions. (a) Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729. (b) Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Lett. 1994, 379. (c) Murakami, M.; Hayashi, M.; Ito, Y. Synlett. 1994, 179. (d) Matsubara, S.; Horiuchi, M.; Takai, K.; Utimoto, K. Chem. Lett. 1995, 259.
27. The silylation of 1-alkynes with chlorosilanes takes place at 120 °C in the presence of commercially available zinc powder: Sugita, H.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 2769.
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33. 3+/Sm = -2.41 V).