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
  • [41] Sequential One-Pot Ruthenium-Catalyzed Azide-Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide
    Johansson, Johan R.
    Lincoln, Per
    Norden, Bengt
    Kann, Nina
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07): : 2355 - 2359
  • [42] On the Mechanism of Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
    Zhu, Lei
    Brassard, Christopher J.
    Zhang, Xiaoguang
    Guha, P. M.
    Clark, Ronald J.
    CHEMICAL RECORD, 2016, 16 (03): : 1501 - 1517
  • [43] Apparent copper(II) catalyzed azide-alkyne cycloaddition
    Brotherton, Wendy S.
    Zhu, Lei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [44] A one-pot protocol for copper-mediated azide-alkyne cycloaddition using alkenyl triflate precursors
    Chen, Yu
    Liu, Lianchao
    Wu, Dimin
    He, Yu-Peng
    Li, Ang
    CHINESE CHEMICAL LETTERS, 2019, 30 (01) : 269 - 270
  • [45] A one carbon staple for orthogonal copper-catalyzed azide-alkyne cycloadditions
    Wright, Karen
    Quinodoz, Pierre
    Drouillat, Bruno
    Couty, Francois
    CHEMICAL COMMUNICATIONS, 2017, 53 (02) : 321 - 323
  • [46] Preparation of highly pure cyclo-polylactides by optimization of the copper-catalyzed azide-alkyne cycloaddition reaction
    Lienard, Romain
    Josse, Thomas
    De Winter, Julien
    Dubois, Philippe
    Gerbaux, Pascal
    Coulembier, Olivier
    POLIMERY, 2017, 62 (04) : 283 - 290
  • [47] Synthesis and functionalization of N-sulfinyl imines: Sonogashira reaction and copper-catalyzed azide-alkyne cycloaddition
    Souza, Frederico B.
    Vasconcelos, Stanley N. S.
    Reis, Joel S.
    Pimenta, Daniel C.
    Stefani, Helio
    TETRAHEDRON LETTERS, 2017, 58 (11) : 1057 - 1060
  • [48] Functionalizing poly(cyclic olefins) using copper-catalyzed azide-alkyne "click" reactions
    Faragher, Robert J.
    McKay, Craig S.
    Hoa, Xuyen D.
    Prikrylova, Barbara
    Lopinski, Gregory P.
    Figeys, Daniel
    Veres, Teodor
    Pezacki, John P.
    CANADIAN JOURNAL OF CHEMISTRY, 2011, 89 (05) : 608 - 615
  • [49] Construction of linear polymers, dendrimers, networks, and other polymeric architectures by copper-catalyzed azide-alkyne cycloaddition "Click" chemistry
    Johnson, Jeremiah A.
    Finn, M. G.
    Koberstein, Jeffrey T.
    Turro, Nicholas J.
    MACROMOLECULAR RAPID COMMUNICATIONS, 2008, 29 (12-13) : 1052 - 1072
  • [50] Raney Ni catalyzed azide-alkyne cycloaddition reaction
    Rao, H. Surya Prakash
    Chakibanda, Guravaiah
    RSC ADVANCES, 2014, 4 (86) : 46040 - 46048
12345