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Volumn 42, Issue 29, 2003, Pages 3412-3414

Nickel-catalyzed dimerization and carbosilylation of 1,3-butadienes with chlorosilanes and Grignard reagents

Author keywords

Dienes; Grignard reagents; Multicomponent reactions; Nickel; Silanes

Indexed keywords

CATALYSIS; DIMERIZATION; NICKEL;

EID: 0042575647     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351579     Document Type: Article
Times cited : (51)

References (26)
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    • 3) coupling reactions of alkyl halides with RMgX: J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; J. Terao, A. Ikumi, H. Kumiyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647.
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    • 3) coupling reactions of alkyl halides with RMgX: J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223; J. Terao, A. Ikumi, H. Kumiyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646-5647.
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    • Terao, J.1    Ikumi, A.2    Kumiyasu, H.3    Kambe, N.4
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    • 2Zn and a ketone, see: a) M. Kimura, S. Matsuo, K. Shibata, Y. Tamaru, Angew. Chem. 1999, 111, 3586-3589; Angew. Chem. Int. Ed. 1999, 38, 3386-3388; b) for reviews of Pd-catalyzed reactions, see: b) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995, pp. 422-449; c) F. Bouachir, P. Grenouillet, D. Neibecker, J. Poirier, I. Tkatchenko, J. Organomet. Chem. 1998, 569, 203-215.
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    • 2Zn and a ketone, see: a) M. Kimura, S. Matsuo, K. Shibata, Y. Tamaru, Angew. Chem. 1999, 111, 3586-3589; Angew. Chem. Int. Ed. 1999, 38, 3386-3388; b) for reviews of Pd-catalyzed reactions, see: b) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995, pp. 422-449; c) F. Bouachir, P. Grenouillet, D. Neibecker, J. Poirier, I. Tkatchenko, J. Organomet. Chem. 1998, 569, 203-215.
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    • 0000460568 scopus 로고    scopus 로고
    • 2Zn and a ketone, see: a) M. Kimura, S. Matsuo, K. Shibata, Y. Tamaru, Angew. Chem. 1999, 111, 3586-3589; Angew. Chem. Int. Ed. 1999, 38, 3386-3388; b) for reviews of Pd-catalyzed reactions, see: b) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995, pp. 422-449; c) F. Bouachir, P. Grenouillet, D. Neibecker, J. Poirier, I. Tkatchenko, J. Organomet. Chem. 1998, 569, 203-215.
    • (1998) J. Organomet. Chem. , vol.569 , pp. 203-215
    • Bouachir, F.1    Grenouillet, P.2    Neibecker, D.3    Poirier, J.4    Tkatchenko, I.5
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    • note
    • Direct reaction with the chlorosilane predominated.
  • 23
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    • For recent reviews of Ni-catalyzed multicomponent coupling reactions, see: a) J. Montgomery, Acc. Chem. Res. 2000, 33, 467-473; b) S. Ikeda, Acc. Chem. Res. 2000, 33, 511-519.
    • (2000) J. Montgomery Acc. Chem. Res. , vol.33 , pp. 467-473
  • 24
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    • For recent reviews of Ni-catalyzed multicomponent coupling reactions, see: a) J. Montgomery, Acc. Chem. Res. 2000, 33, 467-473; b) S. Ikeda, Acc. Chem. Res. 2000, 33, 511-519.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 511-519
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  • 25
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    • (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester
    • Allyl silanes play an important role in organic synthesis as useful intermediates in a number of synthetic transformations; see: T.Y. Luh, S.-T. Liu in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1998, pp. 1793-1868.
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    • and references therein for the Zr-catalyzed silylation of olefins with chlorosilanes see reference [5a]
    • The oxidative addition of chlorosilanes to late transition metals tends to be sluggish as a result of the strong Si-Cl bond energy; see: H. Yamashita, M. Tanaka, M. Goto, Organometallics 1997, 16, 4696-4704, and references therein; for the Zr-catalyzed silylation of olefins with chlorosilanes, see reference [5a].
    • (1997) Organometallics , vol.16 , pp. 4696-4704
    • Yamashita, H.1    Tanaka, M.2    Goto, M.3


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