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Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications
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Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Inorganic Chemistry".

Deadline for manuscript submissions: closed (31 December 2024) | Viewed by 6307

Special Issue Editor

Prof. Dr. Eike Bauer

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St Louis, MO, USA
Interests: organometallic chemistry; iron complexes; catalysts; ligands

Special Issue Information

Dear Colleagues,

Since the discovery of ferrocene’s structure in 1952, the sandwich complexes of iron have intrigued generations of researchers. Over the years, research activities have intensified in the areas of the synthesis of ferrocene derivatives, their structural characterization, their reactivity, redox and electrochemistry, their applications in organic and organometallic synthesis and their use in the wide field of material sciences. Ferrocene and ferrocenium derivatives have been employed as catalysts or reagents (e.g., as oxidants or Lewis acids) in organic transformations. The redox chemistry of ferrocene and its derivatives not only allows for their employment as an electrochemical standard, but also for the investigation of stoichiometric or catalytic electron transfer and electrochemistry. Ferrocene derivatives have been investigated with respect to their cytotoxic activities in bioorganometallic applications. Phosphorus- or heteroatom-substituted ferrocene derivatives can serve as ligands in transition-metal-catalyzed organic reactions. Iron is an abundant and relatively non-toxic base metal, and ferrocene can be easily derivatized, which makes it a good candidate for a variety of applications. This Special Issue aims to compile research on all different aspects of ferrocene chemistry, the synthesis and characterization of their derivatives, their reactivity and electrochemistry and their various applications along the lines described above.

Prof. Dr. Eike Bauer
Guest Editor

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Published Papers (5 papers)

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Research

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16 pages, 4230 KiB  
Article
A Disila[2]ferrocenophane with a Bridging 9,9′-Bi-9H-9-Silafluorene Moiety
by Shinnosuke Usuba, Shogo Morisako, Koichiro Masada, Koh Sugamata and Takahiro Sasamori
Molecules 2025, 30(6), 1361; https://doi.org/10.3390/molecules30061361 - 18 Mar 2025
Viewed by 342
Abstract
A disila[2]ferrocenophane bearing a 9,9′-bi-9H-9-silafluorene (9-silafluorene dimer) moiety as a bridging unit was synthesized and isolated as a stable crystalline compound. Disila[2]ferrocenophane 1, newly obtained in this study, has been characterized by spectroscopic analyses, single crystal X-ray diffraction (SC-XRD) analysis, and [...] Read more.
A disila[2]ferrocenophane bearing a 9,9′-bi-9H-9-silafluorene (9-silafluorene dimer) moiety as a bridging unit was synthesized and isolated as a stable crystalline compound. Disila[2]ferrocenophane 1, newly obtained in this study, has been characterized by spectroscopic analyses, single crystal X-ray diffraction (SC-XRD) analysis, and electrochemical measurements. It was found that the obtained disila[2]ferrocenophane was reduced by a reducing agent to generate the corresponding 1,1′-ferrocenediyl-bis(silylanion) via the reductive Si–Si σ-bond cleavage. The trapping reactions of the 1,1′-ferrocenediyl-bis(silylanion) thus generated with electrophiles have also been attempted. Full article
(This article belongs to the Special Issue Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications)
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12 pages, 4892 KiB  
Article
2-Pyridylmetallocenes, Part IX. Sulphur-Substituted 2-Pyridylferrocene: Synthesis and Reactivity towards Pt(II) and Hg(II)
by Stefan Weigand and Karlheinz Sünkel
Molecules 2024, 29(20), 4884; https://doi.org/10.3390/molecules29204884 - 15 Oct 2024
Cited by 1 | Viewed by 814
Abstract
Thio-substituted 2-pyridylferrocenes [CpFe{C5H3(X)(C5H4N)}] (X = SOTol, 3; SMe, 5) were prepared from [CpFe(C5H4R)] (R = SOTol, 1; 2-C5H4N, 2) in moderate yields. The [...] Read more.
Thio-substituted 2-pyridylferrocenes [CpFe{C5H3(X)(C5H4N)}] (X = SOTol, 3; SMe, 5) were prepared from [CpFe(C5H4R)] (R = SOTol, 1; 2-C5H4N, 2) in moderate yields. The reactions of 3 and 5 with [PtCl2(DMSO)2] yielded the binuclear N, S chelated complexes [CpFe{C5H3(X)(C5H4N)}-(к-N,S)-PtCl2] (X= SOTol, 4, SMe, 6), while the reaction of 5 with Hg(OAc)2/LiCl led to cyclomercuration with generation of [CpFe{C5H2(SMe)(C5H4N)(HgCl)}], 7. The crystal structures of 6·CH2Cl2 and 7 were determined. The structure of 6 showed a weak intramolecular Fe…Pt interaction and several weak intermolecular interactions involving all Cl atoms. Weak intermolecular interactions between Hg and S atoms in the cyclomercurated 7 led to a tetrameric structure involving a Hg2S2 ring. Full article
(This article belongs to the Special Issue Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications)
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Figure 1

21 pages, 2967 KiB  
Article
Cleavage of [Pd2(PP)2(μ-Cl)2][BArF24]2 (PP = Bis(phosphino)ferrocene, BArF24 = Tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) with Monodentate Phosphines
by Ian S. Leiby, Virginia Parparcén, Natalya Ding, Klara J. Kunz, Sadie A. Wolfarth, Jeremiah E. Stevens and Chip Nataro
Molecules 2024, 29(9), 2047; https://doi.org/10.3390/molecules29092047 - 29 Apr 2024
Cited by 1 | Viewed by 1382
Abstract
The addition of Na[BArF24] (BArF24 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) to [Pd(PP)Cl2] (PP = 1,1′-bis(phosphino)ferrocene ligands) compounds results in the loss of a chloride ligand and the formation of the dimeric species [Pd2(PP)2(μ-Cl)2][BArF [...] Read more.
The addition of Na[BArF24] (BArF24 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) to [Pd(PP)Cl2] (PP = 1,1′-bis(phosphino)ferrocene ligands) compounds results in the loss of a chloride ligand and the formation of the dimeric species [Pd2(PP)2(μ-Cl)2][BArF24]2. In most cases, the addition of a monodentate phosphine, PR3, to these dimeric species leads to cleaving of the dimer and formation of [Pd(PP)(PR3)Cl][BArF24]. While these reactions are readily observed via a significant color change, the 31P{1H} NMR spectra offer more significant support, as the singlet for the dimer is replaced with three doublets of doublets. The reaction seems to take place for a wide range of PR3 ligands, although there do appear to be steric limitations to the reaction. The compounds were thoroughly characterized by NMR, and X-ray crystal structures of several of the compounds were obtained. In addition, the ferrocenyl backbone of the 1,1′-bis(phosphino)ferrocene ligands provides an opportunity to examine the oxidative electrochemistry of these compounds. In general, the potential at which oxidations of these compounds occurs shows a dependence on the phosphine substituents. Full article
(This article belongs to the Special Issue Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications)
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Review

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24 pages, 6066 KiB  
Review
Recent Catalytic Applications of Ferrocene and Ferrocenium Cations in the Syntheses of Organic Compounds
by Eike B. Bauer
Molecules 2024, 29(23), 5544; https://doi.org/10.3390/molecules29235544 - 23 Nov 2024
Cited by 1 | Viewed by 1429
Abstract
Ferrocene and its oxidized counterpart, the ferrocenium cation, represent a fascinating class of organometallic compounds with broad utility across various fields, including organic synthesis, pharmaceuticals, and materials science. Over the years, ferrocene, ferrocenium cations, and their derivatives have also gained prominence for their [...] Read more.
Ferrocene and its oxidized counterpart, the ferrocenium cation, represent a fascinating class of organometallic compounds with broad utility across various fields, including organic synthesis, pharmaceuticals, and materials science. Over the years, ferrocene, ferrocenium cations, and their derivatives have also gained prominence for their versatility in catalytic processes. This review article offers an overview of the research of the last decade into ferrocene- and ferrocenium-based catalysis. Key developments are highlighted in catalytic oxidation, cross-coupling, polymerization reactions, and redox-switchable catalysis, as well as the application of ferrocenium cations as Lewis acid catalysts. Full article
(This article belongs to the Special Issue Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications)
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Scheme 1

20 pages, 6482 KiB  
Review
Ansa–Ferrocene Derivatives as Potential Therapeutics
by Marcin Cybulski, Olga Michalak, Włodzimierz Buchowicz and Maria Mazur
Molecules 2024, 29(20), 4903; https://doi.org/10.3390/molecules29204903 - 16 Oct 2024
Cited by 3 | Viewed by 1652
Abstract
It has been known since the 1990s that the introduction of a ferrocenyl–type substituent into compounds with proven biological activity can improve their properties. More recently, it was also shown that a carbon bridge connecting the two cyclopentadienyl rings in ferrocene derivatives could [...] Read more.
It has been known since the 1990s that the introduction of a ferrocenyl–type substituent into compounds with proven biological activity can improve their properties. More recently, it was also shown that a carbon bridge connecting the two cyclopentadienyl rings in ferrocene derivatives could enhance the biological properties of the new compounds compared to those without them. However, the synthesis of ferrocenes with this additional linker, known as ansa–ferrocenes, is more difficult due to advanced synthetic protocols and the phenomenon of planar chirality in ring–substituted compounds. As a result, research into the formation of hybrids, conjugates and other ansa–ferrocene derivatives has not been widely conducted. This review discusses the potential biological properties of these units, covering scientific articles published between 1980 and 2024. Full article
(This article belongs to the Special Issue Ferrocene and Related Iron Complexes: Synthesis, Reactivity and Applications)
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