Magnesiation of electron-rich aryl bromides and their use in nickel-catalyzed cross-coupling reactions

被引:39
|
作者
Lau, Stephen Y. W.
Hughes, Greg
O'Shea, Paul D.
Davies, Ian W.
机构
[1] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Kirkland, PQ H9H 3L1, Canada
[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1021/ol070841b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electron-rich aryl bromides are rapidly converted to the corresponding lithium triarylmagnesiates with (n-Bu)(3)MgLi, which undergo efficient nickel-catalyzed Kumada-Corriu cross-coupling reactions with a variety of aryl and alkenyl bromides, chlorides, tosylates, and triflates.
引用
收藏
页码:2239 / 2242
页数:4
相关论文
共 50 条
  • [21] Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Bromides and Chlorosilanes
    Xing, Mimi
    Cui, Huanhuan
    Zhang, Chun
    ORGANIC LETTERS, 2021, 23 (19) : 7645 - 7649
  • [22] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides
    Qian, Qun
    Zang, Zhenhua
    Wang, Shulin
    Chen, Yang
    Lin, Kunhua
    Gong, Hegui
    SYNLETT, 2013, 24 (05) : 619 - 624
  • [23] Nickel-catalyzed cross-coupling reactions of Aryltitanium(IV) alkoxides with aryl halides
    Manolikakes, Georg
    Dastbaravardeh, Navid
    Knochel, Paul
    SYNLETT, 2007, (13) : 2077 - 2080
  • [24] Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Phosphates with Aryl Bromides
    Ren, Jing-Ao
    Chen, Xue
    Gui, Chao
    Miao, Chengping
    Chu, Xue-Qiang
    Xu, Hao
    Zhou, Xiaocong
    Ma, Mengtao
    Shen, Zhi-Liang
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (15) : 2511 - 2515
  • [25] Nickel-Catalyzed Reductive Cross-Coupling of (Hetero)Aryl Iodides with Fluorinated Secondary Alkyl Bromides
    Li, Xuefei
    Feng, Zhang
    Jiang, Zhong-Xing
    Zhang, Xingang
    ORGANIC LETTERS, 2015, 17 (22) : 5570 - 5573
  • [26] New Progress in Nickel-Catalyzed Aryl-Aryl Cross-Coupling Reactions: A Ligand Survey
    Li, Yongqing
    Cao, Yucai
    Ye, Xiaofeng
    Zhou, Hui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (10) : 1538 - 1552
  • [27] Nickel-Catalyzed Direct Cross-Coupling of Aryl Thioether with Aryl Bromide
    Ma, Na-Na
    Hu, Xuan-Bo
    Wu, Yuan-Shuai
    Zheng, Ya-Wen
    Ma, Mengtao
    Chu, Xue-Qiang
    Xu, Hao
    Luo, Haiqing
    Shen, Zhi-Liang
    ORGANIC LETTERS, 2023, 25 (10) : 1771 - 1775
  • [28] Nickel-catalyzed cross-coupling of aryl chlorides with aryl grignard reagents
    Bohm, Volker P. W.
    Weskamp, Thomas
    Gstottmayr, Christian W. K.
    Herrmann, Wolfgang A.
    1602, Wiley-VCH Verlag (39):
  • [29] Nickel-catalyzed cross-coupling of aryl chlorides with aryl Grignard reagents
    Böhm, VPW
    Weskamp, T
    Gstöttmayr, CWK
    Herrmann, WA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (09) : 1602 - +
  • [30] Nickel-catalyzed stereospecific cross-coupling and reductive coupling reactions
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252