Cross-Coupling of Nonactivated Primary and Secondary Alkyl Halides with Aryl Grignard Reagents Catalyzed by Chiral Iron Pincer Complexes

被引:16
|
作者
Bauer, Gerald [1 ]
Cheung, Chi Wai [1 ]
Hu, Xile [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Inorgan Synth & Catalysis, ISIC LSCI, CH-1015 Lausanne, Switzerland
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 12期
基金
欧洲研究理事会;
关键词
Kumada coupling; iron pincer complex; alkyl halide; aryl Grignard reagent; enantioselectivity; FRIEDEL-CRAFTS REACTION; BEARING BETA-HYDROGENS; PHOSPHINE;
D O I
10.1055/s-0034-1380136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iron(III) bisoxazolinylphenylamido (bopa) pincer complexes are efficient precatalysts for the cross-coupling of nonactivated primary and secondary alkyl halides with phenyl Grignard reagents. The reactions proceed at room temperature in moderate to excellent yields. A variety of functional groups can be tolerated. The enantioselectivity of the coupling of secondary alkyl halides is low.
引用
收藏
页码:1726 / 1732
页数:7
相关论文
共 50 条
  • [1] 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
  • [2] Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents
    Yang, Chu-Ting
    Zhang, Zhen-Qi
    Liang, Jun
    Liu, Jing-Hui
    Lu, Xiao-Yu
    Chen, Huan-Huan
    Liu, Lei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (27) : 11124 - 11127
  • [3] Cross-Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst
    Vechorkin, Oleg
    Godinat, Aurelien
    Scopelliti, Rosario
    Hu, Xile
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) : 11777 - 11781
  • [4] Mild and Phosphine-Free Iron-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides with Alkynyl Grignard Reagents
    Cheung, Chi Wai
    Ren, Peng
    Hu, Xile
    [J]. ORGANIC LETTERS, 2014, 16 (09) : 2566 - 2569
  • [5] Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex
    Martin, R
    Fürstner, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3955 - 3957
  • [6] 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
  • [7] Vanadium-catalyzed cross-coupling reactions of alkyl halides with aryl grignard reagents
    Yasuda, Shigeo
    Yorimitsu, Hideki
    Oshima, Koichiro
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (02) : 287 - 290
  • [8] Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
    Cahiez, Gerard
    Gager, Olivier
    Buendia, Julien
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (07) : 1278 - 1281
  • [9] Iron-catalyzed coupling of aryl grignard reagents with alkyl halides
    Hedstrom, Anna
    Norrby, Per-Ola
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [10] Dinuclear Iron Complex-Catalyzed Cross-Coupling of Primary Alkyl Fluorides with Aryl Grignard Reagents
    Mo, Zhenbo
    Zhang, Qiang
    Deng, Liang
    [J]. ORGANOMETALLICS, 2012, 31 (18) : 6518 - 6521