Preparation of dialkoxyborylbis(bromozincio)methane and its reaction with electrophiles

Chemistry Letters

Volumn , Issue 8, 1999, Pages 747-748

  Matsubara, Seijiro ^a   Otake, Yasuyuki ^a   Hashimoto, Yuko ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033425910     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.747     Document Type: Article

References (18)

1. I. Marek and J.F. Normant, Chem. Rev., 96, 3241 (1996).
2. P. Knochel and J. F. Normant, Tetrahedron Lett., 27, 4427 and 4431 (1986); E. Nakamura, K. Kubota, and G. Sakata, J. Am. Chem. Soc., 119, 5457 (1997); F. Bertini, P. Grasselli, G. Zubiani, and G. Cainelli, Tetrahedron, 26, 1281 (1970); B.J.J. van de Heisteeg, G. Schat, M.A.G.M. Tinga, O.S. Akkerman, and F. Bickelhaupt, Tetrahedron Lett., 27, 6123 (1986).
3. P. Knochel and J. F. Normant, Tetrahedron Lett., 27, 4427 and 4431 (1986); E. Nakamura, K. Kubota, and G. Sakata, J. Am. Chem. Soc., 119, 5457 (1997); F. Bertini, P. Grasselli, G. Zubiani, and G. Cainelli, Tetrahedron, 26, 1281 (1970); B.J.J. van de Heisteeg, G. Schat, M.A.G.M. Tinga, O.S. Akkerman, and F. Bickelhaupt, Tetrahedron Lett., 27, 6123 (1986).
4. P. Knochel and J. F. Normant, Tetrahedron Lett., 27, 4427 and 4431 (1986); E. Nakamura, K. Kubota, and G. Sakata, J. Am. Chem. Soc., 119, 5457 (1997); F. Bertini, P. Grasselli, G. Zubiani, and G. Cainelli, Tetrahedron, 26, 1281 (1970); B.J.J. van de Heisteeg, G. Schat, M.A.G.M. Tinga, O.S. Akkerman, and F. Bickelhaupt, Tetrahedron Lett., 27, 6123 (1986).
5. P. Knochel and J. F. Normant, Tetrahedron Lett., 27, 4427 and 4431 (1986); E. Nakamura, K. Kubota, and G. Sakata, J. Am. Chem. Soc., 119, 5457 (1997); F. Bertini, P. Grasselli, G. Zubiani, and G. Cainelli, Tetrahedron, 26, 1281 (1970); B.J.J. van de Heisteeg, G. Schat, M.A.G.M. Tinga, O.S. Akkerman, and F. Bickelhaupt, Tetrahedron Lett., 27, 6123 (1986).
6. a) K. Takai, T. Kakiuchi, K. Utimoto, J. Org. Chem., 59, 2671 (1994).
7. b) S. Matsubara, T. Mizuno, Y. Otake, M. Kobara, K. Utimoto, and K. Takai, Synlett, 1998, 1369.
8. K. Utimoto, N. Toda, T. Mizuno, M. Kobata, and S. Matsubara, Angew. Chem. Int. Ed. Engl., 36, 2804 (1997).
9. S. Matsubara, Y. Otake, T. Morikawa, and K. Utimoto, Synlett, 1998, 1315.
10. f) S. Matsubara, K. Kawamoto, and K. Utimoto, Synlett, 1998, 267.
11. Boron atom substituted gem-dichromium reagent used for the preparation of alkenylborate from aldehyde. See, K. Takai, N. Shinomiya, H. Kaihara, N. Yosida, T. Moriwake, K. Utimoto, Synlett, 1995, 963.
12. A. Suzuki, Pure Appl. Chem., 63, 419 (1991)
13. M. W. Rathke, E. Chao, and G. Wu, J. Organomet. Chem., 122, 145 (1976).
14. 2, a commercially available Zn from Wako Pure Chemical, which is containing a small amount Pb, is effective. See, Ref 3a.
15. 1H nmr (THF-d8, 0 °C): δ -0.92 (s 1H), 1.14 (s, 12H) ppm.
16. P. Knochel, and R.D. Singer, Chem. Rev., 93, 2117 (1993); P. Knochel, Synlett, 1995, 393.
17. P. Knochel, and R.D. Singer, Chem. Rev., 93, 2117 (1993); P. Knochel, Synlett, 1995, 393.
18. A formation of allylzinc from allylpalladium and diethylzinc: Y. Tamaru, S. Goto, A. Tanaka, M. Shimizu, and M. Kimura, Angew. Chem., Int. Ed. Engl., 35, 878 (1996).