One-Pot Anti-Markovnikov Hydroamination of Unactivated Alkenes by Hydrozirconation and Amination

被引：63
|
作者：
Strom, Alexandra E. [1 ]
Hartwig, John F. [1 ]
机构：
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 17期
关键词：
COPPER-CATALYZED AMINATION; CONVENIENT SYNTHESIS; ORGANIC AZIDES; STEREOSPECIFIC SYNTHESIS; SECONDARY-AMINES; FACILE REACTION; ORGANOBORANES; CHLORAMINE; ALKYL; DIMETHYLALKYLBORANES;
D O I：
10.1021/jo401498w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.
引用
收藏
页码：8909 / 8914
页数：6
相关论文
共 50 条
  • [41] A KI-mediated radical anti-Markovnikov addition of simple ketones/esters to unactivated alkenes
    Tian, Yunfei
    Sun, Changqing
    Tan, Ren Xiang
    Liu, Zhong-Quan
    GREEN CHEMISTRY, 2018, 20 (03) : 588 - 592
  • [42] Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents
    Wagner-Carlberg, Noah
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (49) : 22426 - 22432
  • [43] Nickel-catalysed anti-Markovnikov hydroarylation of unactivated alkenes with unactivated arenes facilitated by non-covalent interactions
    Noam I. Saper
    Akito Ohgi
    David W. Small
    Kazuhiko Semba
    Yoshiaki Nakao
    John F. Hartwig
    Nature Chemistry, 2020, 12 : 276 - 283
  • [44] Nickel-catalysed anti-Markovnikov hydroarylation of unactivated alkenes with unactivated arenes facilitated by non-covalent interactions
    Saper, Noam, I
    Ohgi, Akito
    Small, David W.
    Semba, Kazuhiko
    Nakao, Yoshiaki
    Hartwig, John F.
    NATURE CHEMISTRY, 2020, 12 (03) : 276 - +
  • [45] Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins
    Li, Hongze
    Shen, Shou-Jie
    Zhu, Cheng-Liang
    Xu, Hao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (23) : 9415 - 9421
  • [46] A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes
    Kapat, Ajoy
    Koenig, Andreas
    Montermini, Florian
    Renaud, Philippe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) : 13890 - 13893
  • [47] Photo-induced anti-Markovnikov hydroalkylation of unactivated alkenes employing a dual-component initiator
    Yachao Zhang
    Liang-Liang Mao
    Sifan Hu
    Yi Luan
    Huan Cong
    ChineseChemicalLetters, 2021, 32 (02) : 681 - 684
  • [48] Iodine(Ⅲ) reagent(ABX–N3)-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes
    Xiaonan Li
    Pinhong Chen
    Guosheng Liu
    Science China(Chemistry), 2019, 62 (11) : 1537 - 1541
  • [49] Acceleration of Anti-Markovnikov Hydroamination in the Synthesis of an Active Pharmaceutical Ingredient
    Mitic, Aleksandar
    Skovby, Tommy
    Dam-Johansen, Kim
    Gernaey, Krist V.
    CHEMICAL ENGINEERING & TECHNOLOGY, 2016, 39 (10) : 1821 - 1827
  • [50] Photo-induced anti-Markovnikov hydroalkylation of unactivated alkenes employing a dual-component initiator
    Zhang, Yachao
    Mao, Liang-Liang
    Hu, Sifan
    Luan, Yi
    Cong, Huan
    CHINESE CHEMICAL LETTERS, 2021, 32 (02) : 681 - 684
12345