Nickel-catalyzed cross-coupling of unactivated alkyl halides and tosylate carrying a functional group with alkyl and phenyl Grignard reagents

被引：29
|
作者：
Singh, Surya Prakash [1 ]
Terao, Jun [2 ]
Kambe, Nobuaki [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 40期
关键词：
PD; COMPLEXES; EFFICIENT; NI;
D O I：
10.1016/j.tetlet.2009.07.094
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By the use of catalytic amounts of a nickel salt and a 1,3-butadiene, primary and secondary alkyl Grignard reagents undergo cross-coupling with alkyl bromides, iodide, and tosylate carrying a functional group such as amide, ester, and ketone at 0 degrees C in THF. The present procedure provides a simple, convenient, and practical method for construction of carbon chains in the presence of various functional groups. PhMgBr also gave the corresponding coupling product in a moderate yield. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5644 / 5646
页数：3
相关论文
共 50 条
  • [1] Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides
    Yu, Xiaolong
    Yang, Tao
    Wang, Shulin
    Xu, Hailiang
    Gong, Hegui
    ORGANIC LETTERS, 2011, 13 (08) : 2138 - 2141
  • [2] Nickel-Catalyzed Cross-Coupling of Non-activated and Functionalized Alkyl Halides with Alkyl Grignard Reagents
    Vechorkin, Oleg
    Hu, Xile
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) : 2937 - 2940
  • [3] EFFECTS OF NATURE OF HALIDES ON ALKYL GROUP ISOMERIZATION IN NICKEL-CATALYZED CROSS-COUPLING OF SECONDARY ALKYL GRIGNARD-REAGENTS WITH ORGANIC HALIDES
    KISO, Y
    TAMAO, K
    KUMADA, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 50 (01) : C12 - C14
  • [4] Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
    Gu, Jun
    Qiu, Canbin
    Lu, Wenbin
    Qian, Qun
    Lin, Kunhua
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2017, 49 (08): : 1867 - 1873
  • [5] Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides
    Everson, Daniel A.
    Weix, Daniel J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [6] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
    Everson, Daniel A.
    Shrestha, Ruja
    Weix, Daniel J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) : 920 - +
  • [7] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
    Weix, D. J.
    Everson, D. A.
    Shrestha, R.
    SYNLETT, 2010, (08) : A45 - A46
  • [8] Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents
    Xu, Guoqiang
    Li, Xiaoyan
    Sun, Hongjian
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (18) : 3011 - 3014
  • [9] Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides
    Zhu, Dianhu
    Lv, Leiyang
    Qu, Zihang
    Li, Chao-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6312 - 6322
  • [10] Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant
    Gong, Hegui
    Xu, Hailiang
    Zhao, Chenglong
    Synthesis (Germany), 2013, 45 (23)
12345