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

共 50 条

[21] Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)
Mandoli, Alessandro
MOLECULES, 2016, 21 (09):
[22] INOR 407-Mechanism and modification of the copper-catalyzed azide-alkyne cycloaddition reaction
Finn, M. G.
Rodionov, Valentin
Presolski, Stanislav
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[23] The Janus Face of the X Ligand in the Copper-Catalyzed Azide-Alkyne Cycloaddition
Jin, Liqun
Romero, Erik A.
Melaimi, Mohand
Bertrand, Guy
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) : 15696 - 15698
[24] Thermoresponsive xylan hydrogels via copper-catalyzed azide-alkyne cycloaddition
Pahimanolis, Nikolaos
Sorvari, Anni
Luong, Nguyen Dang
Seppala, Jukka
CARBOHYDRATE POLYMERS, 2014, 102 : 637 - 644
[25] Copper-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Polydiacetylene: "Click Glycoliposome" as Biosensors for the Specific Detection of Lectins
Pernia Leal, Manuel
Assali, Mohyeddin
Fernandez, Inmaculada
Khiar, Noureddine
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) : 1828 - 1836
[26] Influence of halide ions on the rate of a copper-catalyzed azide-alkyne cycloaddition
Womble, Michael D.
Moorman, Rebekah M.
Collier, Matthew B.
Frohock, Bram H.
Chalker, Justin M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[27] Enantioselective Copper-Catalyzed Azide-Alkyne Click Cycloaddition to Desymmetrization of Maleimide-Based Bis(alkynes)
Song, Tao
Li, Li
Zhou, Wei
Zheng, Zhan-Jiang
Deng, Yuan
Xu, Zheng
Xu, Li-Wen
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (02) : 554 - 558
[28] Radiofluorination of an Anionic, Azide-Functionalized Teroligomer by Copper-Catalyzed Azide-Alkyne Cycloaddition
Wenzel, Barbara
Schmid, Maximilian
Teodoro, Rodrigo
Moldovan, Rares-Petru
Lai, Thu Hang
Mitrach, Franziska
Kopka, Klaus
Fischer, Bjoern
Schulz-Siegmund, Michaela
Brust, Peter
Hacker, Michael C.
NANOMATERIALS, 2023, 13 (14)
[29] An efficient one-pot synthesis of C2-symmetric triazolophanes by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction
Rajesh, R.
Periyasami, G.
Raghunathan, R.
TETRAHEDRON LETTERS, 2010, 51 (14) : 1896 - 1898
[30] Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst
Shin, Jung-Ah
Lim, Yeong-Gweon
Lee, Kyung-Hee
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08): : 4117 - 4122

← 1 2 3 4 5 →