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A biferrocenyl ligand containing a pyridinyl moiety which can introduce a degree of flexibility between the metal-binding domains for metallosupramolecules was prepared. The X-ray structural determination and the electrochemical measurement for this new functionalized pyridinyl biferrocene were also reported.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Owing to their fairly high stability under visible irradiation, ferrocene and ferrocenyl derivatives are widely used in luminescent systems. They are classical quenchers of excited states. Both energy and electron transfer may be involved, depending on the nature of the excited species. Inter- or intramolecular quenching are encountered. Applications span from the study of reaction mechanisms to that of organized or biological media. Recently, dyads and polyads designed for their ability to mimic photosynthetic centers or for their photodiode properties have also been obtained. Finally, the incorporation of a ferrocenyl derivative in a luminescent system does not necessarily lead to luminescence quenching. New applications are emerging, in which advantage is taken of the presence of ferrocene acting as a redox center: this gives optically and electrochemically active sensors. The present review encompasses the literature up to November 1999.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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1,1?-Ferrocene biscarboxaldehyde (1) has been prepared and the aldehyde groups were subsequently protected with acetal groups to produce 1,1?-bisacetalferrocene (2). A ring-locked ferrocene was synthesised by further derivatisation of the cyclopentadiene rings at the 2,2? positions with phosphine substituents to produce 2,2?-bis-(acetal)-1,1?-diphenylphosphinoferrocene (3), which was subsequently coordinated to either a nickel chloride (5) or nickel bromide (6) metal centre. The ring-locked ferrocene complexes produced 2,5?-bis-(acetal)-1,1?-diphenylphosphinoferrocene substitution patterns. The acetal protecting groups of 2,2?-bis-(acetal)-1,1?-diphenylphosphinoferrocene were removed to produce 1,1?-bis-carboxaldehyde-2,2?-diphenylphosphinoferrocene (4). The Cp rings of 1,1?-bisacetalferrocene were also further derivatised at the 2,2? positions with a silane to produce the ring-locked 1,1?-siloxane-2,5?-bisacetalferrocenophane (7). The acetal protecting groups were removed from this to produce 1,1?-siloxane-2,5?-ferrocenophanecarboxaldehyde (8). For both the phosphine and siloxane electrophiles, the substitution on the Cp rings gives chiral products (obtained as racemic mixtures). Due to the highly regioselective nature of the reaction and diastereoselectivity in the products only C2-symmetric compounds were observed without the presence of meso diastereoisomers. Subsequent ring-locking forced the Cp rings to rotate, leading to 1,1?-ring-locked ferrocenes with 2,5?-arrangement of the acetal groups (i.e. on opposite faces of the ferrocene unit).

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states. Application In Synthesis of 1,1′-Diacetylferrocene, You can get involved in discussing the latest developments in this exciting area about 1273-94-5

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The ligands 1-ethoxycarbonyl-3-ferrocenyl-propane-1,3-dion and ferrocene-1,1?-bis(2,4-dioxo-butanoic acid ethylester) have been prepared by reaction of acetylferrocene or 1,1?-diacetylferrocene and diethyl oxalate. They yield neutral chelates with CuII, NiII, ZnII, CoII, and MnII. The acid dissociation constants of the ligands and the stability constants of their metal complexes including FeII complexes are reported. The structure of bis(1-ethoxycarbonyl-3-ferrocenyl-propane-1,3-dionato)copper(II) was determined by X-ray structure analysis. A cis arrangement with a nearly square planar coordination sphere at the Cu atom is found.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A series of complexes of transition metal ions (Cr3+, Mn 2+, Co2+, Ni2+, Cu2+, Zn 2+) and of lanthanide ions (La3+, Nd3+, Gd 3+, Dy3+, Lu3+) with the anions of ferrocenylmethyl-L-cysteine [(C5H5)Fe(C5H 4CH(R)SCH2CH(NH3+)CO 2-] (L1) and with the dianions of 1,1?-ferrocenylbis(methyl-L-cysteine) [Fe(C5H 4CH(R)SCH2CH(NH3+) CO 2-)2] (R = H, Me, Ph) (L2) as N,O,S-donors were prepared. With the monocysteine ferrocene derivative L 1 as ligands complexes [MIIL12] or [CrIIIL12]Cl type complexes are formed whereas the bis(cysteine) ligand L2 yields insoluble complexes of type [ML2]n, presumably as coordination polymers. The magnetic moments of [MnIIL2]n, [PrIIIL 2]n(OH)n and [DyIIIL 2]n(OH)n exhibit “normal” paramagnetism.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A novel structure of ferrocene derivative 1 was synthesized with cyanuric chloride and ferrocenemethanol as starting materials. The synthesized compound was fully characterized using 1H NMR, 13C NMR, MS and XRD. Subsequently, the in vitro anticancer effect against A549, HCT116 and MCF-7 cell lines was preliminarily evaluated by the MTT method. The result showed that this compound exhibits good cytotoxic effect on A549, HCT116 and MCF-7 cell lines.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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This account focuses on the application in catalysis of ruthenium and osmium complexes containing 2-(aminomethyl)pyridine (Ampy)-based ligands. The combination of these aminoalkylpyridine ligands with appropriate phosphines affords ruthenium and osmium systems displaying unprecedented high catalytic activity and productivity in a variety of organic transformations such as hydrogenation by hydrogen transfer and dihydrogen, dehydrogenation, racemization, and alkylation.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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We have determined a convenient method for the bulk synthesis of high-purity ferric heme-nitrosyl complexes ({FeNO}6 in the Enemark-Feltham notation); this method is based on the chemical or electrochemical oxidation of corresponding {FeNO}7 precursors. We used this method to obtain the five- and six-coordinate complexes [Fe(TPP)(NO)]+ (TPP2- = tetraphenylporphyrin dianion) and [Fe(TPP)(NO)(MI)]+ (MI = 1-methylimidazole) and demonstrate that these complexes are stable in solution in the absence of excess NO gas. This is in stark contrast to the often-cited instability of such {FeNO}6 model complexes in the literature, which is likely due to the common presence of halide impurities (although other impurities could certainly also play a role). This is avoided in our approach for the synthesis of {FeNO}6 complexes via oxidation of pure {FeNO}7 precursors. On the basis of these results, {FeNO}6 complexes in proteins do not show an increased stability toward NO loss compared to model complexes. We also prepared the halide-coordinated complexes [Fe(TPP)(NO)(X)] (X = Cl-, Br-), which correspond to the elusive, key reactive intermediate in the so-called autoreduction reaction, which is frequently used to prepare {FeNO}7 complexes from ferric precursors. All of the complexes were characterized using X-ray crystallography, UV-vis, IR, and nuclear resonance vibrational spectroscopy (NRVS). On the basis of the vibrational data, further insight into the electronic structure of these {FeNO}6 complexes, in particular with respect to the role of the axial ligand trans to NO, is obtained.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Six symmetrical ferrocenyl Schiff base materials were synthesized and characterized by UV, 1H NMR, mass spectrometry (MS) and elemental analysis. Their off-resonant third-order nonlinear optical properties were measured using femtosecond laser and degenerate four-wave mixing (DFWM) technique. The third-order nonlinear optical susceptibilities chi(3) were 1.961-6.363 × 10-13 esu. The nonlinear refractive indexes n2 were 3.609-11.716 × 10-12 esu. The second-order hyperpolarizabilities gamma of these molecules were 1.967-6.388 × 10-31 esu. The response time were 45.759-73.079 fs. The results indicate that these materials have potential nonlinear optical applications.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Treatment of Fe(eta5-C5H4CH2OH)2 (1) with two equivalents of ClC(O)R (2) (a, R = 2-cC4H3O; b, R = 2-cC4H3S; c, R = 2-cC4H3Se; d, R = 3-cC4H3S) produced the corresponding ferrocenylmethyl carboxylates Fe(eta5-C5H4CH2OC(O)R)2 (3a?d), while the reaction of FcCH2OLi (Fc = Fe(eta5-C5H5)(eta5-C5H4)) with 2,5-(ClC(O))2-cC4H2X (5) (a, X = O; b, X = S; c, X = Se) in a 2:1 molar ratio gave 2,5-(FcCH2OC(O))2-cC4H2X (6a?c). Compounds 3a?d and 6a?c were characterized by elemental analysis, NMR (1H and 13C{1H}) and IR spectroscopy. The molecular structures of 3a,b,d in the solid state were determined by single crystal X-ray structure analysis. Compound 3a crystallizes in the monoclinic space group P21/c, while 3b,d crystallize in the triclinic space group P-1¯. The ester groups and the heteroatoms are in an anti arrangement with respect to each other. Cyclic voltammetry measurements for 3a?d and 6a?c show reversible electrochemical processes (Fc/Fc+) between 165 and 176 mV for 3a?d, and 94 and 116 mV for 6a?cb, using [NnBu4][B(C6F5)4] as the supporting electrolyte. It was found that for 3a, a somewhat higher Fc/Fc+ redox potential (E0?) is observed when compared with the more electron-rich systems 3b,c,d. The molecular electronic structures of the title compounds were additionally investigated by DFT calculations, revealing different degrees of HOMO?LUMO energy gaps within the series, due to a lowering of the LUMO energy, depending on the nature of the heterocyclic ring.

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion