Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents Using a Tetrachloroferrate with an Innocent Countercation

被引:2
|
作者
Hashimoto, Toru [1 ]
Maruyama, Tsubasa [1 ]
Yamaguchi, Takamichi [1 ]
Matsubara, Yutaka [1 ]
Yamaguchi, Yoshitaka [1 ]
机构
[1] Yokohama Natl Univ, Grad Sch Engn, Dept Adv Mat Chem, Hodogaya Ku, 79-5 Tokiwadai, Yokohama, Kanagawa 2408501, Japan
关键词
Iron; ferrate salt; cross-coupling reaction; alkyl halide; Grignard reagent; CATALYZED KUMADA; ALKENYL HALIDES; COMPLEX BEARING; IRON-PHOSPHINE; ATE COMPLEX; REACTIVITY; CHLORIDES; LIGAND; NUCLEOPHILES; BENZYL;
D O I
10.1002/adsc.201900568
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Bis(triphenylphosphoranylidene)ammonium tetrachloroferrate, (PPN)[FeCl4] (1), was evaluated as a catalyst for cross-coupling reactions. 1 exhibits high stability toward air and moisture and is an effective catalyst for the reaction of secondary alkyl halides with aryl Grignard reagents. The PPN cation is considered as an innocent counterpart to the iron center. We have developed an easy-to-handle iron catalyst for "ligand-free" cross-coupling reactions.
引用
收藏
页码:4232 / 4236
页数:5
相关论文
共 50 条
  • [1] Vanadium-catalyzed cross-coupling reactions of alkyl halides with aryl grignard reagents
    Yasuda, Shigeo
    Yorimitsu, Hideki
    Oshima, Koichiro
    Bulletin of the Chemical Society of Japan, 2008, 81 (02): : 287 - 290
  • [2] Vanadium-catalyzed cross-coupling reactions of alkyl halides with aryl grignard reagents
    Yasuda, Shigeo
    Yorimitsu, Hideki
    Oshima, Koichiro
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (02) : 287 - 290
  • [3] Cobalt-catalyzed cross-coupling reactions of alkyl halides with aryl Grignard reagents and their application to sequential radical cyclization/cross-coupling reactions
    Ohmiya, H
    Wakabayashi, K
    Yorimitsu, H
    Oshima, K
    TETRAHEDRON, 2006, 62 (10) : 2207 - 2213
  • [4] Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
    Cahiez, Gerard
    Gager, Olivier
    Buendia, Julien
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (07) : 1278 - 1281
  • [5] Silver-catalyzed cross-coupling reactions of alkyl bromides with alkyl or aryl Grignard reagents
    Someya, Hidenori
    Yorimitsu, Hideki
    Oshima, Koichiro
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3270 - 3272
  • [6] Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents
    Nakamura, M
    Matsuo, K
    Ito, S
    Nakamura, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3686 - 3687
  • [7] Cobalt-catalyzed Cross-coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents
    Hamaguchi, Hiroyuki
    Uemura, Minoru
    Yasui, Hiroto
    Yorimitsu, Hideki
    Oshima, Koichiro
    CHEMISTRY LETTERS, 2008, 37 (11) : 1178 - 1179
  • [8] Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex
    Martin, R
    Fürstner, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3955 - 3957
  • [9] Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents
    Guerinot, Amandine
    Reymond, Sebastien
    Cossy, Janine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) : 6521 - 6524
  • [10] Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents
    Kim, Ju Hyun
    Chung, Young Keun
    CHEMICAL COMMUNICATIONS, 2013, 49 (94) : 11101 - 11103