Kumada-Tamao-Corriu Coupling of Alkyl Halides Catalyzed by an Iron-Bisphosphine Complex

被引:83
作者
Hatakeyama, Takuji [1 ]
Fujiwara, Yu-ichi [1 ,2 ]
Okada, Yoshihiro [1 ,2 ]
Itoh, Takuma [1 ,2 ]
Hashimoto, Toru [1 ,2 ]
Kawamura, Shintaro [1 ,2 ]
Ogata, Kazuki [1 ,2 ]
Takaya, Hikaru [1 ]
Nakamura, Masaharu [1 ]
机构
[1] Kyoto Univ, IRCELS, ICR, Kyoto 6110011, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158530, Japan
基金
日本学术振兴会;
关键词
ARYL GRIGNARD-REAGENTS; BOND FORMATION; PHOSPHATES; SUBSTITUTION; REACTIVITY; COBALT; SALTS;
D O I
10.1246/cl.2011.1030
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iron(II) chloride complex possessing a sterically demanding ortho-phenylene-tethered bisphosphine ligand shows a high catalytic activity in the Kumada-Tamao-Corriu coupling of nonactivated alkyl halides with aryl Grignard reagents. Primary, secondary, and tertiary alkyl halides can participate as an electrophilic coupling partner. A radical clock experiment using (iodomethyl)cyclopropane exclusively gives the corresponding ring-opening coupling product, suggesting intermediacy of alkyl radical species.
引用
收藏
页码:1030 / 1032
页数:3
相关论文
共 43 条
  • [11] Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions
    Czaplik, Waldemar Maximilian
    Mayer, Matthias
    Cvengros, Jan
    Jacobi von Wangelin, Axel
    [J]. CHEMSUSCHEM, 2009, 2 (05) : 396 - 417
  • [12] de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
  • [13] Iron-catalysed sp3-sp3 cross-coupling reactions of unactivated alkyl halides with alkyl Grignard reagents
    Dongol, Krishna G.
    Koh, Huishi
    Sau, Manisankar
    Chai, Christina L. L.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (07) : 1015 - 1018
  • [14] Iron-catalyzed cross-coupling between alkenyl and dienyl sulfonates and functionalized arylcopper reagents
    Dunet, G
    Knochel, P
    [J]. SYNLETT, 2006, (03) : 407 - 410
  • [15] MIXED COUPLING BETWEEN VINYLIC SULFONES AND GRIGNARD-REAGENTS IN THE PRESENCE OF SALTS OF TRANSITION-METALS - STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS
    FABRE, JL
    JULIA, M
    VERPEAUX, JN
    [J]. TETRAHEDRON LETTERS, 1982, 23 (24) : 2469 - 2472
  • [16] Preparation, structure, and reactivity of nonstabilized organoiron compounds.: Implications for iron-catalyzed cross coupling reactions
    Fuerstner, Alois
    Martin, Ruben
    Krause, Helga
    Seidel, Guenter
    Goddard, Richard
    Lehmann, Christian W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8773 - 8787
  • [17] Advances in iron catalyzed cross coupling reactions
    Fürstner, A
    Martin, R
    [J]. CHEMISTRY LETTERS, 2005, 34 (05) : 624 - 629
  • [18] Iron-catalyzed cross-coupling reactions
    Fürstner, A
    Leitner, A
    Méndez, M
    Krause, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) : 13856 - 13863
  • [19] Hatakeyama T., ANGEW CHEM INT EDIT, DOI [10.1021/anie.20114125, DOI 10.1021/ANIE.20114125]
  • [20] Iron-catalyzed selective biaryl coupling: Remarkable suppression of homocoupling by the fluoride anion
    Hatakeyama, Takuji
    Nakamura, Masaharu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) : 9844 - +