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Four organometallic nucleobases have been prepared and characterized, each consisting of a disubstituted ferrocene unit connected through either a conjugated or saturated linker group to adenine or thymine nucleobases. Their assembly behavior has been studied in the solid state via X-ray crystallography, revealing intermolecular H-bonded arrays. The electrode potentials in DCM are strongly dependent upon the nature of the linker group between the ferrocene unit and the nucleobase.

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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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[1+1], [1+2], [2+1] or [3+1] acyclic and [1+1] or [2+2] cyclic Schiff bases (LALS), containing ferrocene moieties, have been prepared by reaction of formyl- or 1,1?-diformylferrocene and the appropriate amines. Formyl- and 1,1-diformylferrocene form respectively the acyclic [2+1] LW and [2+2]n LZ compounds by reaction with 1,4-diaminomethylbenzene. Similar compounds (LTLV) have been obtained by condensation of aminomethylferrocene and 2,6-diformylpyridine, 2,6-diformyl-4-chlorophenol and 3-methoxy-2-hydroxybenzaldehyde. By reduction of these compounds with NaBH4 the corresponding ferrocene-amine derivatives (L?) have been synthesized. All these compounds have been characterized by physico-chemical measurements (IR, NMR, Moessbauer spectroscopy and FAB mass spectrometry) and LH, derived by the condensation of ferrocene-aldehyde and 1,5-diamino-3-oxa-pentane, also by an X-ray structural determination. The X-ray analysis of crystals of LH, grown from a diethyl ether solution, shows that two independent molecules are present in the asymmetric unit; these two molecules are chemically equivalent with the ferrocenyl groups in the eclipsed form. The coordination ability of these compounds towards d metal ions as copper(II), nickel(II), platinum(II) and rhodium(III) was investigated; while the Schiff bases (L) may suffer hydrolysis, their reduced analogues (L?) form stable, well-defined complexes of the type M(L?)(Cl)n (n=2, 3). The Moessbauer spectra of the prepared compounds show signals with delta at 0.44 and DeltaEQ 2.30 mm s-1 for the Schiff bases LALS and 0.52 and 2.40 mm s-1 for the reduced analogues and hence may be diagnostic of the presence of Fe-CH=N- or Fe-CH2-NH- groups. The signals with delta at 0.51-0.55 and DeltaEQ at 2.34-2.38 mm s-1 for the Schiff bases LTLV, having Fe-CH2-N=CH groups, resemble those of the reduced analogues.

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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 effects of a direct connection between ferrocene and porphyrin units have been thoroughly investigated by electrochemical and spectroscopic methods. These data not only reveal that substitution of the porphyrin macrocycle by one, two, three or four ferrocenyl groups strongly affects the electronic properties of the porphyrin and ferrocenyl moieties, they also clearly demonstrate that the metallocene centres are “connected” through the porphyrin-based electronic network. The dynamic properties of selected ferrocene-porphyrin conjugates have been investigated by VT NMR and metadynamic calculations. 1,3-Dithiolanyl protecting groups have been introduced on the upper rings of the ferrocene fragments to allow a straightforward and easy access to redox active picket-fence porphyrins. X-ray diffraction analyses of the zinc(ii) 5-[1?-[2-(1,3-dithiolanyl)]ferrocenyl]-10,15,20-tri(p-tolyl)porphyrin and 5,15-bis[1?-[2-(1,3-dithiolanyl)]ferrocenyl]-10,20-bis(p-tolyl)porphyrin complexes reveal the existence of S-Zn bonds involved in supramolecular arrays. The solid state analysis of the trans-5,15-di-(1?-(formyl)ferrocenyl)-10, 20-di-(p-tolyl)-porphyrinatozinc(ii) complex, obtained by deprotection of the dithiolane substituted analog, is conversely found in the crystal lattice as a monomer exhibiting a hexacoordinated zinc metal centre. The Royal Society of Chemistry 2013.

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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 synthesis of a C2 symmetric 1,1? ,2,2?-tetrasubstituted ferrocene system was discussed. The route involved the reduction of ferrocenyl carbonyl compounds which gave access to a range of alcohols, alkenes, alkanes, ethers, and 2-oxa[3]ferrocenophanes depending on the precise conditions used. The loss of optical activity of 1,1?-bis(hydroxymethyl)ferrocenes and 1,1?-bis(hydroxymethyl)ruthenocenes, which had been prepared by asymmetric reduction, was demonstrated in an acidic medium by extensive 1H NMR studies.

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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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Lithioferrocene, 1,1′-dilithioferrocene, lithioruthenocene and 1,1′-dilithioruthenocene all react with N,N-dimethylformamide in diethyl ether to produce the respective aldehydes.The lithiation of the two metallocenes can be steered to maximize the formation of only one of the two aldehydes by choosing either n-butyllithium in the presence of tetramethylethylenediamine (TMEDA) or t-butyllithium (tBuLi) as the metallating reagent: ferrocene mono-aldehydes or 1,1′-dialdehydes are formed with good yields (91percent and 85percent respectively, based on ferrocene), lower yields (50percent) of ruthenocene-1,1′-dialdehyde were obtained under the standard conditions, because the 1,3,1′-trialdehyde also formed in significant (19percent) amounts.Monolithiation by nBuLi and the formation of the ruthenocene monoaldehyde (yield, 66percent) are favoured when TMEDA is used in only catalytic amounts; lithiation of ruthenocene by tBuLi selectively leads to monolithioruthenocene and the mono-aldehyde (yield, 91percent).The products are easily purified by column chromatography.The simplicity and the high yield of these reactions make them much more desirable than the previously known multistep procedures.

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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 potassium bis-dithiocarbamate (bis-dtc) salts of 1,3- bis(benzylaminomethyl)benzene (1,3-Bn-ambdtc), 1,3-bis(iso-butylaminomethyl) benzene (1,3-iBu-ambdtc), 1,4-bis(benzylaminomethyl)benzene (1,4-Bn-ambdtc), and 1,4-bis(iso-butylaminomethyl)benzene (1,4- iBu-ambdtc) were reacted with three different diorganotin dichlorides (R2SnCl2 with R = Me, nBu, and Ph) in 1:1 stoichiometric ratios to give the corresponding diorganotin bis- dithiocarbamates. Additionally, the dimethyltin bis-dithiocarbamate of 1,1?-bis(benzylaminomethyl)ferrocene (1,1?-Bn-amfdtc) was prepared. The resulting complexes have been characterized as far as possible by elemental analysis, FAB+ mass spectrometry, IR and NMR (1H, 13C, and 119Sn) spectroscopy, and single-crystal X-ray diffraction, showing that the tin complexes are dinuclear 24- and 26-membered macrocyclic species of composition [{R2Sn(bis-dtc)}2]. As shown by 119Sn NMR spectroscopy, the tin centers are hexa-coordinated in all cases; however, two different coordination environments are possible, as detected by single-crystal X-ray diffraction. In the dimethyltin derivatives of 1,3-Bn-ambdtc, 1,3-iBu-ambdtc, 1,4-Bn-ambdtc, and 1,1?-Bn-amfdtc and the di-n-butyltin derivative of 1,3- iBu-ambdtc, the metal atoms are embedded in skewed-trapezoidal- bipyramidal coordination polyhedra with asymmetrically coordinating trans-oriented dtc groups. In contrast, in the diphenyltin derivative 1,3- iBu-ambdtc, the metal centers have distorted octahedral coordination with symmetrically coordinating cis-oriented dtc functions. Thus, for the complexes derived from 1,3-Bn/iBu-ambdtc, two different macrocyclic structures were observed. In the dimethyl- and di-n-butyltin derivatives, the bridging bis-dtc ligands adopt U-shaped conformations, while in the case of the diphenyltin derivative, the conformation is L-shaped. Furthermore, two different macrocyclic ring conformations can occurr, which differ in the spatial orientation of the substituents attached to the nitrogen atoms (Bn or iBu). The dimethyltin derivatives of 1,4-Bn-ambdtc and 1,1?-Bn-amfdtc have cavities, in which aromatic rings are accomodated in the solid state.

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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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Barbier-type gamma-regiospecific allylation of formylferrocene (1) with allyl bromides in the presence of stannous chloride dihydrate and catalytic cupric chloride in dichloromethane-water (1:1) afforded corresponding ferrocenyl dienes FcCHC(R1)C(R2)CH2 (3-6). On the other hand, similar reactions of 1,1?-bis-formylferrocene (2) yielded oxa-bridged [3]-ferrocenophanes having allyl pendants Fc[CH2C(R2)CH(R1)CH-mu(O)-CHCH (R1)C(R2)CH2] (8-11). The latter appear to result from the dehydration of intermediate homoallylic alcohols. Dehydration could be arrested in case of reaction of 1 and 2 with 1-bromo-3-methyl-but-2-ene, which results in the formation of homoallylic alcohols FcCH(OH)C(Me2)CHCH2 (7) and Fc[CH(OH)C(Me2)CHCH2]2 (12), respectively. All the reactions completely fail in absence of water.

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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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A family of ferrocene-functionalised receptors of different topologies have been used as receptors for anions. The compounds have been designed to contain both amine nitrogen and ether oxygen atoms and comprises from monoaza to pentaaza derivatives both open-chain (L1, L2, L3) or cyclic (L4, L5) and having from one to five ferrocenyl groups. Solution studies directed to determine the protonation constants of L1, L2 and L3 have been carried out in water (0.1 mol dm3 KNO3, 25 C) and those of L4 and L5 in 1,4-dioxane-water (70:30 v/v, 0.1 mol dm-3 KNO3, 25 C). The protonation behaviour of the receptors can be explained taking into account electrostatic considerations. Speciation studies in the presence of phosphate have been carried out in water for L’, L2 and L3 and in dioxane-water for L4 and L5. Speciation studies have also been performed in the presence of ATP with L1, L2 and L3 in water. Selectivity of a mixture of receptors against a certain anion is discussed in terms of ternary diagrams. The shift of the redox potential of the ferrocenyl groups as a function of the pH has been studied. The difference between the oxidation potentials at basic and acidic pH has been determined experimentally and is compared with that theoretically predicted using an electrostatic model previously reported. The electrochemical shift in the presence of ATP and phosphate has been measured in water for L1, L2 and L3 and in the presence of phosphate and sulfate in 1,4-dioxane-water for L4 and L5 as a function of the pH. The electrochemical response found against those anions is quite poor with maximum cathodic shifts off. 30tO mV. The electrochemical response induced by HSO4 and H2PO4- has also been studied in acetonitrile solutions where a large cathodic shift for H2PO4- up to ca. 200 mV was found. The Royal Society of Chemistry 2000.

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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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A simple and efficient protocol is developed for the preparation of bibrachial chiral heterodentate ligands bearing two amino acid or peptide side chains on different scaffolds. Copyright

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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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Cocrystals derived from 1,1?-bis(ethenyl-4-pyridyl)ferrocene (1) and resorcinol/phloroglucinol and a crystal of 1,1?-bis-(ethenyl-4-quinolinyl)ferrocene (5) have been studied with the aim of engineering crystalline NLO materials. X-ray structure analyses revealed a NLO active syn-type molecular conformation of 1 and 5 via hydrogen bonding with resorcinol/phloroglucinol and pi-pi interaction between quinoline rings, respectively. For 5, all molecular dipoles are aligned in the same direction and the SHG efficiency is about 4 times that of urea. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

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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