Synthesis, characterization and electrochemical properties of 3-ferrocenylbenzoxaboroles

Publication date: Available online 4 November 2019Source: Journal of Organometallic ChemistryAuthor(s): Krzysztof M. Borys, Maria B. Jaworska, Agata Kowalczyk, Anna M. Nowicka, Agnieszka Adamczyk-WoźniakAbstract3-Ferrocenylbenzoxaboroles are organoboron compounds combining the structural features of diol-binding benzoxaborole with redox-active ferrocene. Herein, a two-step method for the preparation of these hitherto unreported compounds is described. First, ferrocenecarboxaldehyde is transformed into 2-halo-1-ferrocenylbenzyl alcohols via halogen-selective transmetallation. Next, the obtained alcohols are subjected to palladium-catalyzed borylation, affording the title benzoxaboroles. All compounds have been characterized spectroscopically by means of NMR and FTIR, and their purity confirmed by elemental analysis. Cyclic voltammetry studies have allowed for the determination of the redox potentials, diffusion coefficients and electron-transfer rate constants of the studied electroactive species.Graphical abstract

Source: Journal of Organometallic Chemistry - November 6, 2019 Category: Chemistry Source Type: research