Kumada Cross-Coupling of Aryl Grignard Reagents with Aryl Halides Catalyzed by an Immobilized Nickel Catalyst

被引：8
|
作者：
Chen, Xiaofang [1 ]
Wang, Lei [1 ,2 ]
Liu, Jie [1 ]
机构：
[1] Huaibei Coal Teachers Coll, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2009年 / 14期
关键词：
Kumada cross-coupling; immobilized nickel(II) complex; bidentate nitrogen ligands; Grignard reagents; aryl halides; INORGANIC HYBRID MATERIALS; CARBON-CARBON BONDS; REUSABLE CATALYST; HIGHLY EFFICIENT; HETEROGENEOUS CATALYST; ON-CHARCOAL; C-C; PALLADIUM; SILICA; SONOGASHIRA;
D O I：
10.1055/s-0029-1216832
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Kumada cross-coupling reaction of a variety of unactivated aryl bromides and aryl chlorides with phenylmagnesium bromide has been developed. The reaction is catalyzed by an immobilized nickel(II) complex containing a pyrrolidine unit, which is part of a bidentate nitrogen ligand. The catalyst is highly efficient for the Kumada reaction, which proceeds smoothly at 10 degrees C to generate the corresponding products in good to excellent yields. In addition, the catalyst can be reused five times without significant loss of activity.
引用
收藏
页码：2408 / 2412
页数：5
相关论文
共 50 条
  • [21] Dinuclear Systems in the Efficient Nickel-Catalyzed Kumada-Tamao-Corriu Cross-Coupling of Aryl Halides
    Matsubara, Kouki
    Yamamoto, Hitomi
    Miyazaki, Satoshi
    Inatomi, Takahiro
    Nonaka, Keita
    Koga, Yuji
    Yamada, Yuji
    Veiros, Luis F.
    Kirchner, Karl
    [J]. ORGANOMETALLICS, 2017, 36 (02) : 255 - 265
  • [22] Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides
    Zhang, Qingchen
    Wang, Xuan
    Qian, Qun
    Gong, Hegui
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (17): : 2829 - 2836
  • [23] NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING .1. CROSS-COUPLING OF ALKYL, ARYL, AND ALKENYL GRIGNARD-REAGENTS WITH ARYL AND ALKENYL HALIDES - GENERAL SCOPE AND LIMITATIONS
    TAMAO, K
    SUMITANI, K
    KISO, Y
    ZEMBAYASHI, M
    FUJIOKA, A
    KODAMA, S
    NAKAJIMA, I
    MINATO, A
    KUMADA, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (07) : 1958 - 1969
  • [24] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
    Weix, D. J.
    Everson, D. A.
    Shrestha, R.
    [J]. SYNLETT, 2010, (08) : A45 - A46
  • [25] Cross-Coupling of Aryl/Alkenyl Ethers with Aryl Grignard Reagents through Nickel-Catalyzed C-O Activation
    Xie, Lan-Gui
    Wang, Zhong-Xia
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (18) : 4972 - 4975
  • [26] Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides
    Everson, Daniel A.
    Weix, Daniel J.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [27] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
    Everson, Daniel A.
    Shrestha, Ruja
    Weix, Daniel J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) : 920 - +
  • [28] Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents
    Yu, Da-Gang
    Li, Bi-Jie
    Zheng, Shu-Fang
    Guan, Bing-Tao
    Wang, Bi-Qing
    Shi, Zhang-Jie
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) : 4566 - 4570
  • [29] CROSS-COUPLING OF ARYL HALIDES WITH GRIGNARD-REAGENTS CATALYZED BY IODO(PHENYL)BIS(TRIPHENYLPHOSPHINE)-PALLADIUM(II)
    SEKIYA, A
    ISHIKAWA, N
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 118 (03) : 349 - 354
  • [30] PHOSPHINE-NICKEL COMPLEX CATALYZED CROSS-COUPLING OF GRIGNARD-REAGENTS WITH ARYL AND ALKENYL HALIDES - 1,2-DIBUTYLBENZENE
    KUMADA, M
    TAMAO, K
    SUMITANI, K
    [J]. ORGANIC SYNTHESES, 1988, 50-9 : 407 - 411
12345