Publication details

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

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.
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