N-alkylation of N-heterocyclic ionic liquid precursors in ionic liquids

被引：7
|
作者：
Ruether, Thomas [1 ]
Ross, Tamsyn [1 ]
Mensforth, Emily J. [1 ]
Hollenkamp, Anthony Frank [1 ]
机构：
[1] CSIRO Energy Technol, Clayton, Vic 3169, Australia
来源：
GREEN CHEMISTRY | 2009年 / 11卷 / 06期
关键词：
REDUCTIVE AMINATION; TRANSITION-METAL; TERTIARY-AMINES; HALIDES; ALDEHYDES; KETONES; CHEMOSELECTIVITY; REACTIVITY;
D O I：
10.1039/b817526h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The room temperature ionic liquids [BMIM][PF6] and [P14][Tf2N] in conjunction with KOH are superior reaction media for the alkylation of the secondary amine 3-azabicyclo[3.2.2] nonane under mild conditions. The factors examined were alkyl halide chain length (C1 to C4) and halide identity (Cl, Br, I). The tertiary amine products are released from the reaction medium as a separate layer and can be isolated in good yields by simple decantation.
引用
收藏
页码：804 / 809
页数：6
相关论文
共 50 条
  • [41] Nanoclusters in ionic liquids: Evidence for N-heterocyclic carbene formation from imidazolium-based ionic liquids detected by 2H NMR
    Ott, Lisa Starkey
    Cline, Morgan L.
    Deetlefs, Maggel
    Seddon, Kenneth R.
    Finke, Richard G.
    Journal of the American Chemical Society, 2005, 127 (16): : 5758 - 5759
  • [42] Liquid-solid phase change absorption of SO2 by N-heterocyclic ionic liquid
    Xie, Xuhao
    Chen, Ling
    Xu, Shengchao
    Zhao, Wenbo
    Huagong Jinzhan/Chemical Industry and Engineering Progress, 2019, 38 (12): : 5603 - 5611
  • [43] N-Heterocyclic Carbenes, Ionic Liquids, and Reactive Small Molecules: A Conversation between a Student and His Professor
    Land, Michael A.
    Clyburne, Jason A. C.
    SYNLETT, 2016, 27 (17) : 2416 - 2424
  • [44] Stability and organocatalytic efficiency of N-heterocyclic carbenes electrogenerated in organic solvents from imidazolium ionic liquids
    Feroci, Marta
    Chiarotto, Isabella
    D'Anna, Francesca
    Forte, Gianpiero
    Noto, Renato
    Inesi, Achille
    ELECTROCHIMICA ACTA, 2015, 153 : 122 - 129
  • [45] An Operationally Simple and Scalable Approach to Functionalized Ionic Liquids from Phosphonium and N-Heterocyclic Halide Salts
    Meyer, Christopher J.
    Vogt, Monika
    Catalino, James P.
    Ashfeld, Brandon L.
    SYNLETT, 2013, 24 (11) : 1428 - 1432
  • [46] O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids
    Talisman, Ian Jamie
    Kumar, Vineet
    Razzaghy, Jacqueline
    Malhotra, Sanjay V.
    CARBOHYDRATE RESEARCH, 2011, 346 (07) : 883 - 890
  • [47] Chemical and thermal stability of N-heterocyclic ionic liquids in catalytic C-H activation reactions
    Chen, Guanyi
    Kang, Shujuan
    Ma, Qisheng
    Chen, Weiqun
    Tang, Yongchun
    MAGNETIC RESONANCE IN CHEMISTRY, 2014, 52 (11) : 673 - 679
  • [48] N-Alkylation and N,C-Dialkylation of Amines with Alcohols in the Presence of Ruthenium Catalysts with Chelating N-Heterocyclic Carbene Ligands
    Sahin, Zeynel
    Gurbuz, Nevin
    Ozdemir, Ismail
    Sahin, Onur
    Buyukgungor, Orhan
    Achard, Mathieu
    Bruneau, Christian
    ORGANOMETALLICS, 2015, 34 (11) : 2296 - 2304
  • [49] Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes
    Liu, Dajiang
    Zhang, Yuetao
    Chen, Eugene Y. -X.
    GREEN CHEMISTRY, 2012, 14 (10) : 2738 - 2746
  • [50] Syntheses of N-heterocyclic carbene precursors
    Burgess, Kevin
    CHEMISTRY & INDUSTRY, 2008, (12) : 27 - 27
12345