Electronic Effects on the Depropargylation Process in the Reaction‐based Fluorescent Detection of Palladium Species: Benzocoumarin‐based Ratiometric Sensing Systems,Bulletin of the Korean Chemical Society

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Electronic Effects on the Depropargylation Process in the Reaction‐based Fluorescent Detection of Palladium Species: Benzocoumarin‐based Ratiometric Sensing Systems
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2020-12-29 , DOI: 10.1002/bkcs.12173
Seo Won Cho ₁ , Ye Jin Reo ₁ , Sourav Sarkar ₁ , Kyo Han Ahn ₁

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The palladium catalyzed cross‐coupling reactions are indispensable in organic synthesis of pharmaceutical compounds, demanding convenient tools for the analysis of residual palladium contents. Propargyl aryl ether‐type fluorescent sensing systems that detect Pd(0)/Pd(II)/Pd(IV) species through depropargylation require no additives. We investigated a ratiometric sensing system based on a benzocoumarin dye; thus, three propargyl aryl ethers bearing electronically‐different self‐immolative linkers were synthesized and their relative response rate toward Pd(0) and Pd(II) were compared. We found that the response rate became faster when the self‐immolative linker became more electron‐deficient. The best‐performing system sensed Pd(0)/Pd(II) species selectively against various other metal species, which is also capable of fluorescent imaging of Pd(0)/Pd(II) species in cells. The work provides us a clue to accelerate the catalytic depropargylation step, which, when combined with a novel fluorophore, would enable us to develop out‐performing palladium sensing systems.

中文翻译：

基于反应的荧光检测钯物种中脱炔丙基化过程的电子效应：基于苯并香豆素的比率传感系统

钯催化的交叉偶联反应在药物化合物的有机合成中必不可少，因此需要方便的工具来分析残留的钯含量。炔丙基芳基醚型荧光传感系统可通过去炔丙基化来检测Pd（0）/ Pd（II）/ Pd（IV）物质，无需任何添加剂。我们研究了一种基于苯并香豆素染料的比例传感系统；因此，合成了三个带有电子不同自消灭性连接基的炔丙基芳基醚，并比较了它们对Pd（0）和Pd（II）的相对响应率。我们发现，当自焚连接体变得越来越缺乏电子时，响应速度就会加快。表现最佳的系统可选择性地检测Pd（0）/ Pd（II）物种对其他各种金属物种，它也能够对细胞中的Pd（0）/ Pd（II）物种进行荧光成像。这项工作为我们提供了加速催化脱炔丙基化步骤的线索，当与新型荧光团结合使用时，它将使我们能够开发出性能卓越的钯传感系统。

更新日期：2021-01-27

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