1,2-Migration of phosphorus-centered anions on ate-type copper carbenoids and its application for the synthesis of new potent phosphine ligands

Organic Letters

Volumn 7, Issue 25, 2005, Pages 5713-5715

  Kondo, Junichi ^a   Someya, Hidenori ^a   Kinoshita, Hidenori ^a   Shinokubo, Hiroshi ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 29444434713     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052520a     Document Type: Article

References (34)

1. (a) Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
2. (b) Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994.
3. (c) Lipshutz, B. H. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 2002; p 665.
4. (a) Phenylsulfanyl: Posner, G. H.; Whitten, C. E.; Sterling, J. J. J. Am. Chem. Soc. 1973, 95, 7788.
5. (b) N-Imidazolyl: Lipshutz, B. H.; Fatheree, P.; Hagen, W.; Stevens, K. L. Tetrahedron Lett. 1992, 33, 1041.
6. (a) Bertz, S. H.; Dabbagh, G.; Villacorta, G. M. J. Am. Chem. Soc. 1982, 104, 5824.
7. (b) Bertz, S. H.; Dabbagh, G. J. Org. Chem. 1984, 49, 1119.
8. (c) Martin, S. F.; Fishpaugh, J. R.; Power, J. M.; Giolando, D. M.; Jones, R. A.; Nunn, C. M.; Cowley, A. H. J. Am. Chem. Soc. 1988, 110, 7226.
9. (a) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 11109.
10. (b) Kondo, J.; Ito, Y.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 106.
11. (c) Kondo, J.; Inoue, A.; Ito, Y.; Shinokubo, H.; Oshima, K. Tetrahedron 2005, 61, 3361.
12. We recently described new methods for the synthesis of organophosphorus compounds. See: (a) Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4873.
13. (b) Sato, A.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 1694.
14. (c) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 2368.
15. We could not detect the byproduct, α,α- bis(methyldiphenylsilyl)-acetonitrile, which was derived via 1,2-migration of the cyano group.
16. Classical synthetic methods of silylmethyl- and bis(silyl) methylphosphines were reported. See: (a) Appel, R.; Schoeler, H. F. Chem. Ber. 1979, 112, 1068.
17. (b) Holmes-Smith, R. D.; Osei, R. D.; Stobart, S. R. J. Chem. Soc., Perkin Trans. 1 1983, 861.
18. (c) Appel, R.; Haubrich, G.; Knoch, F. Chem. Ber. 1984, 117, 2063.
19. (d) Wolfsberger, W. Chemiker Zeitung 1989, 113, 349.
20. (e) Kawashima, T.; Mitsuda, N.; Inamoto, N. Bull. Chem. Soc. Jpn. 1991, 64, 708.
21. (f) Bennett, M. A.; Edwards, A. J.; Harper, J. R.; Khimyak, T.; Willis, A. C. J. Organomet. Chem. 2001, 629, 7.
22. (g) Wang, L.; Chen, X.; Huang, S.; Liu, D. Shanxi Daxue Xuebao, Ziran Kexueban 2004, 27, 160.
23. (a) Allen, D. W.; Taylor, B. F. J. Chem. Soc., Dalton Trans. 1982, 51.
24. (b) Socol, S. M.; Verkade, J. G. Inorg. Chem. 1984, 23, 3487.
25. (c) Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
26. (d) Niyomura, O.; Iwasawa, T.; Sawada, N.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Organometallics 2005, 24, 3468.
27. (e) The selenide of 9a was prepared according to the reported procedure in ref 7a.
28. Tolman, C. A. Chem. Rev. 1977, 77, 313.
29. Transition-metal-catalyzed reactions with dendritic phosphine ligands containing silylmethylphosphine units were reported. See: Benito, M.; Rossell, O.; Seco, M.; Muller, G.; Ordinas, J. I.; Font-Bardia, M.; Solans, X. Eur. J. Inorg. Chem. 2002, 2477.
30. Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Soc. Chem. 1999, 121, 2123.
31. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
32. (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
33. (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
34. (b) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085 and references therein.