1,1′-Bis(3-hydroxypropyl)ferrocene: Preparation and substitution with polyfluoroalkyl groups

SiMe3CH2CH2 was demonstrated as a robust and convenient OH protecting group in the preparation of 1,1′-bis(3-hydroxypropyl)ferrocene (1). The OH groups were used to introduce polyfluorinated alkyl chains by acylation of 1 with (C2F5CO)2O and alkylation with CF3(CF2)6CH2OH under Mitsunobu reaction conditions. This demonstrates a new method for introduction of an ω-hydroxyalkyl group to the Cp unit as a synthetic handle for modification of molecular properties.

Graphical abstractThe hydroxy groups in ferrocene derivative 1 are explored as a synthetic handle for the introduction of polyfluoroalkyl substituents.Figure optionsDownload full-size imageDownload as PowerPoint slide