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
  • [31] IRON CATALYZED CROSS-COUPLING REACTIONS - SYNTHESIS OF ARYLETHENES
    MOLANDER, GA
    RAHN, BJ
    SHUBERT, DC
    BONDE, SE
    [J]. TETRAHEDRON LETTERS, 1983, 24 (49) : 5449 - 5452
  • [32] Iron-catalyzed Grignard cross-coupling with alkyl halides possessing β-hydrogens
    Nagano, T
    Hayashi, T
    [J]. ORGANIC LETTERS, 2004, 6 (08) : 1297 - 1299
  • [33] Low-Valent Iron-Catalyzed C-C Bond Formation-Addition, Substitution, and C-H Bond Activation
    Nakamura, Eiichi
    Yoshikai, Naohiko
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) : 6061 - 6067
  • [34] Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents
    Nakamura, M
    Matsuo, K
    Ito, S
    Nakamura, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3686 - 3687
  • [35] Nakamura M., 2010, PCT Int. Appl, Patent No. [WO2010/001640A1, 2010001640]
  • [36] Effect of TMEDA on Iron-Catalyzed Coupling Reactions of ArMgX with Alkyl Halides
    Noda, Daisuke
    Sunada, Yusuke
    Hatakeyama, Takuji
    Nakamura, Masaharu
    Nagashima, Hideo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) : 6078 - +
  • [37] Plietker B., 2008, IRON CATALYSIS ORGAN
  • [38] New cobalt- and iron-catalyzed reactions of organozinc compounds
    Reddy, CK
    Knochel, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15): : 1700 - 1701
  • [39] Iron-catalyzed aryl-aryl cross-couplings with magnesium-derived copper reagents
    Sapountzis, I
    Lin, WW
    Kofink, CC
    Despotopoulou, C
    Knochel, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1654 - 1657
  • [40] The Promise and Challenge of Iron-Catalyzed Cross Coupling
    Sherry, Benjamin D.
    Fuerstner, Alois
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1500 - 1511