Publication details
Unexpected reactivity of ferrocenyl-iminoboronates: Breaking ortho-imine bonds by oxidation in the presence of non-aqueous sodium chloride
| Authors | |
|---|---|
| Year of publication | 2020 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron Letters |
| MU Faculty or unit | |
| 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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