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

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[1] Vural Gürsel, Iris
[2] Aldiansyah, Ferry
[3] Wang, Qi
[4] Noël, Timothy
[5] Hessel, Volker
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Noël, Timothy (t.noel@tue.nl) | 1600年 / Elsevier B.V., Netherlands卷 / 270期
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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;
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