Highly regioselective silaboration of 3-substituted 1,2-dienes catalyzed by palladium/2,6-xylyl isocyanide

Synlett

Volumn , Issue 10, 1999, Pages 1567-1568

  Suginome, Michinori ^a   Ohmori, Yutaka ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

2 boryl allylsilane; Allenes; Palladium 2,6 xylyl isocyanide; Regioselectivity; Silaboration

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; STEREOCHEMISTRY;

EID: 0032843570     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2917     Document Type: Article

References (24)

1. (a) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948.
2. (b) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487.
3. (c) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608.
4. (d) Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061.
5. (e) Suginome, M.; Nakamura, H.; Ito, Y. Tetrahedron Lett. 1997, 38, 555.
6. (f) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096.
7. (g) Suginome, M.; Ito, Y. J. Chem. Soc., Dalton Trans. 1998, 1925.
8. (a) Suginome, M.; Nakamura, H.; Ito, Y. Chem. Commun. 1996, 2777.
9. (b) Suginome, M.; Matsuda, T.; Nakamura, H.; Ito, Y. Tetrahedron 1999, 55, 8787.
10. Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem. 1997, 109, 2627; Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
11. Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem. 1997, 109, 2627; Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
12. Suginome, M.; Nakamura, H.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 1998, 120, 4248.
13. Suginome, M.; Matsuda, T.; Ito, Y. Organometallics 1998, 17, 5233.
14. Transition metal-catalyzed bismetalation reactions of 1,2-dienes have been reported. For Si-Si, see: (a) Watanabe, H.; Saito, M.; Sutou, N.; Nagai, Y. J. Chem. Soc., Chem. Commun. 1981, 617.
15. (b) Watanabe, H.; Saito, M.; Sutou, N.; Kishimoto, K.; Inose, J.; Nagai, Y. J. Organomet. Chem. 1982, 225, 343.
16. For Sn-Sn, see: (c) Killing, H.; Mitchell, T. N. Organometallics 1984, 3, 1318.
17. (d) Mitchell, T. N.; Schneider, U. J. Organomet. Chem. 1991, 407, 319.
18. For Si-Sn, see: (e) Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J. Chem. Soc., Chem. Commun. 1985, 354.
19. For B-B, see: (f) Ishiyama, T.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1998, 39, 2357.
20. 2Si: C, 73.88; H, 8.68. Found: C, 73.71; H, 8.88.
21. 3, 75 MHz) δ -4.3, -3.3, 13.8, 14.1, 22.3, 22.9, 24.3, 24.9, 29.7, 30.7, 31.1, 82.6, 127.5, 128.5, 134.1, 140.1, 144.8.
22. 3, 75 MHz) δ -3.3, 24.3, 24.8, 25.9, 26.0, 34.0, 39.4, 82.7, 127.5, 128.7, 133.9, 139.8, 151.7.
23. 2Si: C, 44.53; H, 4.23. Found: C, 44.33; H, 4.12.
24. 3, 75 MHz) δ -3.3, 25.2, 114.3, 123.4, 127.0, 127.8, 129.2, 133.5, 137.9, 144.4, 146.8, 149.2.