Synthesis of Selectively Mono-N-Arylated Aliphatic Diamines via Iridium-Catalyzed Amine Alkylation

被引：105
|
作者：
Blank, Benoit [1 ]
Michlik, Stefan [1 ]
Kempe, Rhett [1 ]
机构：
[1] Univ Bayreuth, Lehrstuhl Anorgan Chem 2, D-95440 Bayreuth, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期
关键词：
amine alkylation; amino alcohols; diamines; iridium; ASTERISK-IR COMPLEX; BORROWING HYDROGEN; REDUCTIVE AMINATION; TERTIARY-AMINES; ALCOHOLS; SECONDARY; HYDROAMINATION; HETEROCYCLIZATION; ACTIVATION; COORDINATION;
D O I：
10.1002/adsc.200900548
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly selective phosphorus/nitrogen (P,N) ligand-based iridium catalyst system efficiently catalyzes the reaction of arylamines with unprotected amino alcohols, yielding N-arylated aliphatic diamines in yields of up to 93%. The reaction can be performed with a wide variety of branched and linear amino alcohols in combination with various aminopyridines or substituted anilines.
引用
收藏
页码：2903 / 2911
页数：9
相关论文
共 50 条
  • [1] Iridium-catalyzed N-alkylation of diamines with glycerol
    Crotti, Corrado
    Farnetti, Erica
    Licen, Sabina
    Barbieri, Pierluigi
    Pitacco, Giuliana
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 382 : 64 - 70
  • [2] The Iridium-Catalyzed Synthesis of Symmetrically and Unsymmetrically Alkylated Diamines under Mild Reaction Conditions
    Michlik, Stefan
    Hille, Toni
    Kempe, Rhett
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (05) : 847 - 862
  • [3] Selective Iridium-Catalyzed Alkylation of (Hetero) Aromatic Amines and Diamines with Alcohols under Mild Reaction Conditions
    Blank, Benoit
    Michlik, Stefan
    Kempe, Rhett
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (15) : 3790 - 3799
  • [4] The Synthesis of Benzimidazoles and Quinoxalines from Aromatic Diamines and Alcohols by Iridium-Catalyzed Acceptorless Dehydrogenative Alkylation
    Hille, Toni
    Irrgang, Torsten
    Kempe, Rhett
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (19) : 5569 - 5572
  • [5] Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination
    Wang, Jing
    Wang, Wenji
    Yang, Xiongyu
    Liu, Jingwen
    Huang, Haizhou
    Chang, Mingxin
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (02) : 518 - 525
  • [6] Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination
    Jing Wang
    Wenji Wang
    Xiongyu Yang
    Jingwen Liu
    Haizhou Huang
    Mingxin Chang
    Science China Chemistry, 2023, 66 : 518 - 525
  • [7] Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation
    Hethcox, J. Caleb
    Shockley, Samantha E.
    Stoltz, Brian M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (28) : 8664 - 8667
  • [8] Recent Advances in Iridium-Catalyzed Alkylation of C-H and N-H Bonds
    Pan, Shiguang
    Shibata, Takanori
    ACS CATALYSIS, 2013, 3 (04): : 704 - 712
  • [9] Iridium-Catalyzed Decarboxylative N-Alkylation of α-Amino Acids with Primary Alcohols
    Wu, Jiashou
    Jiang, Huajiang
    Chen, Dingben
    Shen, Jianfen
    Zhao, Datong
    Xiang, Jing
    Zhou, Qizhong
    SYNLETT, 2014, 25 (04) : 539 - 542
  • [10] Mechanistic study on the Cp*iridium-catalyzed N-alkylation of amines with alcohols
    Zhao, Guo-Ming
    Liu, Hui-ling
    Huang, Xu-ri
    Zhang, Dan-dan
    Yang, Xue
    RSC ADVANCES, 2015, 5 (29) : 22996 - 23008
12345