Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride

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Authors	KONHEFR Martin MICHALCOVÁ Lenka SKRUTKOVÁ LANGMAJEROVÁ Monika GLATZ Zdeněk SKLÁDAL Petr MAZAL Ctibor LACINA Karel
Year of publication	2020
Type	Article in Periodical
Magazine / Source	Tetrahedron Letters
MU Faculty or unit	Faculty of Science
Citation
Web	https://www.sciencedirect.com/science/article/pii/S0040403919313346
Doi	http://dx.doi.org/10.1016/j.tetlet.2019.151535
Keywords	Ferrocene; Boronic acid; Electrochemically facilitated interaction; Alkali metal complexation; Imine bond
Description	The boronic acid moiety in the proximity of electron-donating structures in ((ferrocenylimino)methyl)phenylboronic acid 1 significantly improves the reactivity of the molecule. The ortho regioisomer 1a exhibits a two-fold higher affinity to NaCl compared to its meta 1b and para 1c isomers, respectively. Moreover, the double imine bond in 1a was broken by the interaction with NaCl in methanol upon activation by electrochemical oxidation.
Related projects:	CEITEC 2020 ROS-Induced Drug Release Based on Interactions of Ferrocenylboronates Podpora biochemického výzkumu v roce 2020