Ferrocenes with perfluorinated side chains and ferrocenophanes with fluorinated handles

Max Roemer, Youn Kyung Kang, Young Keun Chung, Dieter Lentz*

*Corresponding author for this work

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Trifluorovinyl groups are introduced onto the cyclopentadienyl ligands of ferrocene at the 1-, 1,1′-, and 1,2-positions by Negishi-type and Stille-type coupling reactions of trifluorovinylzinc chloride and tri-n-butyltrifluorovinyl stannane with several iodoferrocenes. Modification of the trifluorovinyl group by nucleophilic substitution and [2+2] cycloaddition make them versatile building blocks for synthetic transformations. 1,1′-Bis(trifluorovinyl) ferrocene reacts upon contact with silica or oxidizing agents and in the presence of a suitable nucleophile through a redox autocatalytic mechanism to afford ferrocenophanes with fluorinated handles. C(F)(H) and C(F)(OMe) moieties in α-positions allowed further modifications to be performed by nucleophilic substitution of the fluorine atoms. A series of ferrocenes with fluorinated side chains and ferrocenophanes with fluorinated handles were isolated and characterized. Several molecular structures were determined by single-crystal X-ray diffraction. The influence of the fluorine substituents on the redox properties of the iron center were studied by cyclic voltammetry.

Original languageEnglish
Pages (from-to)3371-3389
Number of pages19
JournalChemistry - A European Journal
Volume18
Issue number11
DOIs
Publication statusPublished - 12 Mar 2012
Externally publishedYes

Keywords

  • C-C coupling
  • cycloaddition
  • ferrocene
  • fluorine
  • homogeneous catalysis

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