化学
钯
赫克反应
催化作用
三氟甲磺酸
组合化学
磷化氢
反应性(心理学)
乙酰苯胺
有机化学
医学
病理
替代医学
作者
Yi Tan,Marine Lefèvre,François Pierrard,Mathieu Soetens,Maria Shoueiry,Esra Yıldız,Sébastien Ibanez,Kübra Özkan,Olivier Féron,Raphaël Frédérick,Olivier Riant
标识
DOI:10.1016/j.jorganchem.2023.122743
摘要
The palladium-catalyzed uncaging of alloc-protected amines in living cells has been extensively studied mostly in the form of nanostructures or mesostructures. However, the scarcity of kinetic and mechanistic studies of discrete palladium complexes for deallylation reactions has hindered progress. Herein, we report the development of a series of discrete palladium complexes bearing acetanilide ligands, which exhibit a good balance between reactivity and stability in living cells. We investigated the catalytic activity and cytotoxicity of these complexes in SiHa cells and found that acetanilide[tri(2-furyl)phosphine]palladium(II) triflate showed promising results. Under physiological conditions, this palladium complex exhibited a second-order reaction rate of 30 M−1 s−1, and liquid chromatography-mass spectrometry (LC-MS) studies suggested the possibility of a tandem Heck/Tsuji-Trost mechanism. Our results demonstrate the potential of using these discrete palladium complexes for bioorthogonal chemistry studies in living cells.
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