Cobalt-Catalyzed Three-Component Coupling Reaction of Alkyl Halides, 1,3-Dienes, and Trimethylsilylmethylmagnesium Chloride

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3959-3961

  Mizutani, Keiya ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 BIS(DIPHENYLPHOSPHINO)HEXANE; ALKENE DERIVATIVE; ALKYL GROUP; BROMINE DERIVATIVE; CHLORIDE; COBALT; HALIDE; HEXANE; SILANE DERIVATIVE; SILYLMETHYLMAGNESIUM CHLORIDE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 0242628394     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0356643     Document Type: Article

References (25)

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14. For reviews on multicomponent-coupling reactions, see: (a) Weber, L.; Illgen, K.; Almetetter, M. Synlett 1999, 366. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
15. A mixture of stereoisomer (E/Z = 40/60) was employed. The geometry of the starting material seems not to be essential. The use of the pure E-isomer provided almost the same result.
16. 2/dpph, i.e., whether dpph acts as a bidentate or monodentate ligand to the cobalt center.
17. 2MgCl and could not obtain the corresponding coupling products.
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22. For the formation of allylmetals via the addition of alkyl radicals to 1,3-dienes, see: (a) Takai, K.; Matsukawa, N.; Takahashi, A.; Fujii, T. Angew. Chem., Int. Ed. 1998, 37, 152. (b) Terao, J.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1998, 39, 9697. (c) Nii, S.; Terao, J.; Kambe, N. J. Org. Chem. 2000, 65, 5291.
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24. For coupling reactions involving allylcobalt species, see: (a) Gomes, P. ; Gosmini, C.; Périchon, J. J. Org. Chem. 2003, 68, 1142. (b) Gomes, P.; Gosmini, C.; Périchon, J. Org. Lett. 2003, 5, 1043. See also ref 1e.
25. For coupling reactions involving allylcobalt species, see: (a) Gomes, P. ; Gosmini, C.; Périchon, J. J. Org. Chem. 2003, 68, 1142. (b) Gomes, P.; Gosmini, C.; Périchon, J. Org. Lett. 2003, 5, 1043. See also ref 1e.