Continuous metal scavenging and coupling to one-pot copper-catalyzed azide-alkyne cycloaddition click reaction in flow

被引：0
|
作者：
机构：
[1] Vural Gürsel, Iris
[2] Aldiansyah, Ferry
[3] Wang, Qi
[4] Noël, Timothy
[5] Hessel, Volker
来源：
Noël, Timothy (t.noel@tue.nl) | 1600年 / Elsevier B.V., Netherlands卷 / 270期
关键词：
Increasing usage of catalytic chemistry calls for efficient removal of metal traces. This paper describes the development and optimization of a scavenger-based extraction in flow to remove metal catalysts. It enables liquid-liquid extraction with slug flow and phase separation with a porous fluoropolymer membrane. The use of this unit for copper scavenging of various copper sources from organic solvent was studied. The effects of scavenger type (EDTA; DTPA; EDDS); concentration and pH were also investigated. Such analysis allowed to achieve extraction performance as high as 99% at pH of the scavenger solution adjusted to 9.4 and molar ratio of scavenger to copper of 10. Process integration is achieved by coupling this unit downstream to a flow reaction using homogeneous metal-based catalysis; i.e. presenting a continuous uninterrupted metal scavenging unit. The copper-catalyzed azide-alkyne cycloaddition click reaction is studied in one-pot eliminating the need to isolate and handle potentially explosive azide. The triazole product is attained in flow with high yield of up to 92% with 30. min residence time. The level of purity requirement for pharmaceuticals is met in one stage of extraction. © 2015 Elsevier B.V;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Journal article (JA)
引用
收藏
相关论文
共 50 条
  • [11] The mechanism of copper-catalyzed azide-alkyne cycloaddition reaction: A quantum mechanical investigation
    Ozen, Cihan
    Tuzun, Nurcan S.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2012, 34 : 101 - 107
  • [12] Chemically Directed Assembly of Photoactive Metal Oxide Nanoparticle Heterojunctions via the Copper-Catalyzed Azide-Alkyne Cycloaddition "Click" Reaction
    Cardiel, Allison C.
    Benson, Michelle C.
    Bishop, Lee M.
    Louis, Kacie M.
    Yeager, Joseph C.
    Tan, Yizheng
    Hamers, Robert J.
    ACS NANO, 2012, 6 (01) : 310 - 318
  • [13] Chemically directed assembly of photoactive metal oxide nanoparticle heterojunctions via the copper-catalyzed azide-alkyne cycloaddition "click" reaction
    Cardiel, Allison C.
    Benson, Michelle C.
    Bishop, Lee M.
    Louis, Kacie
    Yeager, Joseph
    Tan, Yizheng
    Hamers, Robert J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [14] Peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition.
    Punna, S
    Kuzelka, J
    Wang, Q
    Finn, MG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U387 - U387
  • [15] Ultrasound-Promoted Copper-Catalyzed Azide-Alkyne Cycloaddition
    Cravotto, Giancarlo
    Fokin, Valery V.
    Garella, Davide
    Binello, Arianna
    Boffa, Luisa
    Barge, Alessandro
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01): : 13 - 15
  • [16] Relative Performance of Alkynes in Copper-Catalyzed Azide-Alkyne Cycloaddition
    Kislukhin, Alexander A.
    Hong, Vu P.
    Breitenkamp, Kurt E.
    Finn, M. G.
    BIOCONJUGATE CHEMISTRY, 2013, 24 (04) : 684 - 689
  • [17] Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation
    Hong, Vu
    Presolski, Stanislav I.
    Ma, Celia
    Finn, M. G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9879 - 9883
  • [18] Advancements in the mechanistic understanding of the copper-catalyzed azide-alkyne cycloaddition
    Berg, Regina
    Straub, Bernd F.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2715 - 2750
  • [19] Conditional Copper-Catalyzed Azide-Alkyne Cycloaddition by Catalyst Encapsulation
    Breve, Tobias G.
    Filius, Mike
    Araman, Can
    van der Helm, Michelle P.
    Hagedoorn, Peter-Leon
    Joo, Chirlmin
    van Kasteren, Sander, I
    Eelkema, Rienk
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (24) : 9340 - 9344
  • [20] Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation
    Hong, Vu P.
    Presolski, Stanislav I.
    Ma, Celia
    Finn, M. G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
12345