Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1,2-bis(diphenylphosphino)benzene

被引:85
作者
Hatakeyama, Takuji [1 ]
Kondo, Yoshiyuki [1 ]
Fujiwara, Yu-ichi [1 ]
Takaya, Hikaru [1 ]
Ito, Shingo [2 ]
Nakamura, Eiichi [2 ]
Nakamura, Masaharu [1 ]
机构
[1] IRCELS, Inst Chem Res, Kyoto 6110011, Japan
[2] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
关键词
SECONDARY ALKYL-HALIDES; CROSS-COUPLINGS; GRIGNARD-REAGENTS; LIQUID-CRYSTALS; ARYLATION; CHLORIDES;
D O I
10.1039/b820879d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic amount of 1,2-bis(diphenylphosphino) benzene (DPPBz) achieves selective cleavage of sp(3)-carbon-halogen bond in the iron-catalysed cross-coupling between polyfluorinated arylzinc reagents and alkyl halides, which was unachievable with a stoichiometric modifier such as TMEDA; the selective iron-catalysed fluoroaromatic coupling provides easy and practical access to poly-fluorinated aromatic compounds.
引用
收藏
页码:1216 / 1218
页数:3
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共 37 条
  • [11] Iron-catalyzed alkylations of aromatic Grignard reagents
    Cahiez, Gerard
    Habiak, Vanessa
    Duplais, Christophe
    Moyeux, Alban
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (23) : 4364 - 4366
  • [12] Iron-catalyzed Sonogashira reactions
    Carril, Monica
    Correa, Arkaitz
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) : 4862 - 4865
  • [13] Iron-catalyzed N-arylation of nitrogen nucleophiles
    Correa, Arkaitz
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8862 - 8865
  • [14] Trifluorinated liquid crystals for TFT displays
    Demus, D
    Goto, Y
    Sawada, S
    Nakagawa, E
    Saito, H
    Tarao, R
    [J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1995, 260 : 1 - &
  • [15] An efficient synthesis of diaryl ketones by iron-catalyzed arylation of aroyl cyanides
    Duplais, C
    Bures, F
    Sapountzis, I
    Korn, TJ
    Cahiez, G
    Knochel, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (22) : 2968 - 2970
  • [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] 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
  • [18] Amino alcohols as ligands for nickel-catalyzed Suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids
    González-Bobes, F
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) : 5360 - 5361
  • [19] Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents
    Guerinot, Amandine
    Reymond, Sebastien
    Cossy, Janine
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) : 6521 - 6524
  • [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 - +