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

[Display omitted] •Enhanced reactivity of ortho-isomer of ((ferrocenylimino)methyl)phenylboronic acid 1a.•Chelation of sodium cations with 1a.•Decomposition of oxidized 1a in the presence of NaCl in methanol.•Reaction mechanism of such decomposition based on spectroelectrochemical experiments. The b...

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Published inTetrahedron letters Vol. 61; no. 9; p. 151535
Main Authors Konhefr, Martin, Michalcová, Lenka, Skrutková Langmajerová, Monika, Glatz, Zdeněk, Skládal, Petr, Mazal, Ctibor, Lacina, Karel
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 27.02.2020
Subjects
Alkali metal complexation
Boronic acid
Electrochemically facilitated interaction
Ferrocene
Imine bond
Alkali metal complexation
Electrochemically facilitated interaction
Boronic acid
Ferrocene
Imine bond
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Summary:[Display omitted] •Enhanced reactivity of ortho-isomer of ((ferrocenylimino)methyl)phenylboronic acid 1a.•Chelation of sodium cations with 1a.•Decomposition of oxidized 1a in the presence of NaCl in methanol.•Reaction mechanism of such decomposition based on spectroelectrochemical experiments. 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 meta1b and para1c isomers, respectively. Moreover, the double imine bond in 1a was broken by the interaction with NaCl in methanol upon activation by electrochemical oxidation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151535