Day: March 22, 2021

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Ruthenium(II) complexes containing a phosphine-functionalized thiosemicarbazone ligand: Synthesis, structures and catalytic C-N bond formation reactions via N-alkylation

A series of ruthenium(II) complexes incorporating a thiosemicarbazone chelate tethered with a diphenylphosphine pendant have been studied. Thus, [(PNS-Et)RuCl(CO)(PPh3)] (1), [N,S-(PNS-Et)RuH(CO)(PPh3)2] (2) and [(PNS-Et)RuCl(PPh3)] (3) were synthesized by reactions of various RuII precursors with 2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone (PNS-Et). However, complexation of PNS-Et with an equimolar amount of [RuCl2(dmso)4] resulted in two different entities [(PNS-Et)RuCl(dmso)2] (4) and [(PNS-Et)2Ru] (5) with different structural features in a single reaction. All the RuII complexes have been characterized by analytical and various spectroscopic techniques. Compounds 1-5 were recrystallized, and the X-ray crystal structures have been reported for 1, 2 and 5. In the complexes 1 and 3-5 the ligand coordinated in a tridentate monobasic fashion by forming PNS five- and six-membered rings, whereas in 2, the ligand coordinated in a bidentate monobasic fashion by forming a strained NS four-membered ring. Furthermore, compounds 1-5 showed catalytic activity in N-alkylation of heteroaromatic amines. Notably, complexes 1-3 were found to be very efficient catalysts toward N-alkylation of a wide range of heterocyclic amines with alcohols. In the presence of a catalytic amount of 2 with 50 mol% of KOH, N1,C5-dialkylation of 4-phenylthiazol-2-amine has been investigated. Reaction of in situ generated aldehyde with amine yields the N1,C5-dialkylated products through the hydride ion transformation from alcohol. Complexes 1-3 also catalyzed a variety of coupling reactions of benzyl alcohols and sulfonamides, which were realized often with 99% isolated yields. Advantageously, only one equivalent of the primary alcohol was consumed in the process.

Ruthenium(II) complexes containing a phosphine-functionalized thiosemicarbazone ligand: Synthesis, structures and catalytic C-N bond formation reactions via N-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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Kinetics of the electron self-exchange and electron-transfer reactions of the (trimethylammonio)methylferrocene host-guest complex with cucurbit[7]uril in aqueous solution

The electron self-exchange rate constants for the (trimethylammonio) methylferrocene(+/2+) couple (FcTMA+/2+) have been measured in the absence and presence of the cucurbit[7]uril (CB[7]) host molecule in aqueous solution, using 1H NMR line-broadening experiments. The very strong binding of the ferrocene to CB[7] results in slow exchange of the guest on the NMR time scale, such that resonances for both the free and bound forms of the reduced ferrocene can be observed. The extents of line broadening in the resonances of the two forms of the guest in the presence of the FcTMA 2+ species can be monitored independently, allowing for the determination of the rate constants for the possible self-exchange pathways involving the bound and free forms of both the oxidized and reduced members of the redox couple. The encapsulation of both the reduced and oxidized forms of the ferrocene increases the rate constant (25C) from (2.1 ¡À 0.1) ¡Á 106 M-1 s-1 (for FcTMA+/2+) to (6.7 ¡À 0.7) ¡Á 106 M-1 s-1 (for {FcTMA-CB[7]}+/2+), whereas inclusion of the reduced form only decreases the rate constant to (6 ¡À 1) ¡Á 105 M -1 s-1. The changes in the exchange rate constants upon inclusion of the reactants are related to the effects of CB[7] acting as an outer, second-coordination sphere and are compared to those observed previously for the electron-exchange process in the presence of beta-cyclodextrin and p-sulfonated calix[6]arene hosts. The binding of FcTMA+ and hydroxymethylferrocene to CB[7] significantly reduces the rate constants for their oxidations by the bis(2,6-pyridinedicarboxylato)cobaltate(III) ion (which does not bind to CB[7]) as a result of reduced thermodynamic driving forces and steric hindrance to close approach of the oxidant to the encapsulated ferrocenes.

Kinetics of the electron self-exchange and electron-transfer reactions of the (trimethylammonio)methylferrocene host-guest complex with cucurbit[7]uril in aqueous solution

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Reference£º
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

 

Reference of 1271-51-8, A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 1271-51-8, Name is Vinylferrocene, molecular formula is C12H3Fe. In a Article£¬once mentioned of 1271-51-8

Synthesis, structure, and redox chemistry of ethenyl and ethynyl ferrocene polyaromatic dyads

A series of ferrocenyl-arene dyads, Fc-C=C-Ar, trans-Fc-CH=CH-Ar, and Fc-CH=CH-CH=CH-Ar (Ar = phenyl, 1-naphthyl, 2-naphthyl, 9-phenanthryl, 9-anthryl, 1-pyrenyl, 3-perylenyl) have been synthesized. Their structures and spectroelectrochemical properties are discussed. The molecular structures of several have been determined by X-ray diffraction and the observed structures compared with global free-energy minimized calculated structures. In the solid state all ethynyl dyads have the aromatic ring orthogonal to the ferrocenyl cyclopentadienyl rings, whereas calculations predict a coplanar orientation. Calculated and observed structures agree for the ethenyl dyads with the rings orthogonal and coplanar for the anthryl and pyrenyl dyads, respectively. In most cases the solid-state structures are stabilized by offset pi-stacking interactions between the polycyclic hydrocarbon rings. The two bands in the electronic spectra of the neutral dyads are due to the individual aryl and ferrocenyl end-groups. Upon oxidation at the [Fc]+/0 couple, the ferrocenyl transition is replaced by LMCT bands at lower energy and a new weak band in the NIR assigned to a Fc+ ?aryl transition; these assignments are supported by resonance Raman spectra, and the energy of the Fc+? aryl transition correlates with the ionization energy of the aryl group. These are therefore electrochromic dyads.

Synthesis, structure, and redox chemistry of ethenyl and ethynyl ferrocene polyaromatic dyads

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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

 

Chemistry is traditionally divided into organic and inorganic chemistry. COA of Formula: C12H10FeO2, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 1271-48-3

[PhP(S)(NMeNH2)2]ZnCl2: A Reagent for the Synthesis of Polymetallic Complexes. X-ray Structure of the Electroactive Compound [PhP(S)(NMeN=CHC5H4FeCp)2]ZnCl2

The zinc complex [PhP(S)(NMeNH2)2]ZnCl2 (2), cleanly obtained by reaction of the phosphodihydrazide PhP(S)(NMeNH2)2 (1) with ZnCl2, is a good reagent in producing new polymetallic compounds by condensation reaction with aldehydes. The reaction of 2 with terephthalaldehyde (3) in a 2/1 or 1/1 stoichiometry leads selectively to the acyclic zinc compound [C6H4-1,4-(CH=NNMePhP(S)NMeNH2)2][ZnCl2]2 (6) or to the macrocyclic zinc complex [PhP(S)C6H4-1,4-(CH=NNMe)2]2[ZnCl2]2 (7). Reaction of compound 2 with 2 equiv of ferrocenecarbaldehyde affords the zinc-iron phosphodihydrazone complex [PhP(S)(NMeN=CHC5H4FeCp)2]ZnCl2 (8) whose structure has beendetermined by X-ray crystallography. Crystal data: triclinic P1-, with a = 12.798(1) A, b = 14.639(2) A, c = 11.744(2) A, alpha =111.74(1)¡ã, beta = 115.92(1)¡ã, gamma = 68.36(1)¡ã, V = 1780.9 A**3, Z = 2; R = 0.037, Rw = 0.044 for 3345 observations and 448 variable parameters. In this neutral trimetallic complex, the Zn(II) center adopts a pseudotetrahedral geometry. This structure is characterized by a five-membered ring with the Zn(II) bonded to the S atom and to one of the N atoms of the phosphodihydrazone ligand PhP(S)(NMeN=CHC5H4FeCp)2 (9). Variable-temperature NMR investigations of 8 show that 9 can act as a hemilabile ligand toward ZnCl2 through an exchange process between the two hydrazone arms in solution. Electrochemical study ofcomplex 8, when compared to the ferrocenyl ligand 9, shows that ZnCl2 complexation induces a shift of 80 mV toward a more anodic potential. Reaction of 2 with the ferrocene-1,1′-dicarbaldehyde also produces the bisferrocenyl dizinc macrocycle [Fe(C5H4CH=NNMePhP(S)NMeN=CHC5H4)2Fe][ZnCl2]2 (10).

[PhP(S)(NMeNH2)2]ZnCl2: A Reagent for the Synthesis of Polymetallic Complexes. X-ray Structure of the Electroactive Compound [PhP(S)(NMeN=CHC5H4FeCp)2]ZnCl2

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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

 

Application of 1273-86-5, A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 1273-86-5, Name is Ferrocenemethanol, molecular formula is C11H3FeO. In a Article£¬once mentioned of 1273-86-5

Applications of metallocenes in rechargeable lithium batteries for overcharge protection

One problem encountered in the development of rechargeable lithium batteries is protection of individual cells from overcharging. In this work the addition of metallocene derivatives to cell electrolytes to provide overcharge protection was investigated. Eleven ferrocene derivatives were studied in terms of their redox potentials and mass transport properties in electrochemical cells and ‘AA’ size Li/LixMnO2 rechargeable cells employing 1M LiAsF6 in 50/50 volume percent propylene carbonate/ethylene carbonate (PC/EC) as the electrolyte. The chemical and electrochemical properties of these metallocene derivatives were also studied in terms of the chemical stability of the derivatives toward cell components and electrochemical reversibility in long-term cycling studies. It was found that adsorption of one derivative, dimethylaminomethylferrocene, on the LixMnO2 electrode (DeltaGads = -3.8 Kcal mol-1 based on the Langmuir adsorption isotherm), blocked the intercalation of Li+ ions into the LixMnO2 electrode.

Applications of metallocenes in rechargeable lithium batteries for overcharge protection

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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

 

Related Products of 1271-51-8, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.1271-51-8, Name is Vinylferrocene, molecular formula is C12H3Fe. In a article£¬once mentioned of 1271-51-8

Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts

An asymmetric synthesis of various trifluoromethyl cyclopropanes from olefins, such as vinyl ferrocene, vinyl ethers, vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(ii)-Pheox catalysts. This catalytic system can function at a low catalyst loading (3 mol%) compared with those reported previously, and the desired cyclopropane products are obtained in high yields with excellent diastereoselectivity (up to >99:1) and enantioselectivity (up to 97% ee).

Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(ii)-Pheox catalysts

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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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Synthesis and characterization of 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes. Crystal structures of [Fe{(eta5-C5H4)-C(C6H 5){double bond, long}N-CH2C6H4CH3-4} 2] and 2[Fe{(eta5-C5H4)-CH2N (CH3)…

Title full: Synthesis and characterization of 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes. Crystal structures of [Fe{(eta5-C5H4)-C(C6H 5){double bond, long}N-CH2C6H4CH3-4} 2] and 2[Fe{(eta5-C5H4)-CH2N (CH3)-C6H4OCH3-4}2] ¡¤ 1/4H2O. Direct or catalytic condensation of diacylferrocenes (acyl = formyl, acetyl, and benzoyl) and anilines or benzylamines with titanium tetrachloride as a catalyst resulted in the corresponding diimines 1-3, respectively. Reduction of these imines with sodium borohydride or lithium aluminum hydride/aluminum chloride in THF yielded 1,1?-bis[(N-phenyl)aminomethyl(ethyl)]ferrocenes (4, 5) and 1,1?-bis[(N-benzyl)aminobenzyl]ferrocenes (6), respectively. Reductive methylation of 4-6 with aqueous formaldehyde, cyanoborohydride and acetic acid only afforded 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes (7, 8). 1,1?-Bis[{(N-methyl-N-benzyl)amino}benzyl]ferrocenes (9) were not obtained, probably due to their debenzylation under the acidic conditions. The molecular structures of 3g and 7a were determined by single crystal X-ray analysis.

Synthesis and characterization of 1,1?-bis[(N-methyl-N-phenyl)aminomethyl(ethyl)]ferrocenes. Crystal structures of [Fe{(eta5-C5H4)-C(C6H 5){double bond, long}N-CH2C6H4CH3-4} 2] and 2[Fe{(eta5-C5H4)-CH2N (CH3)…

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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

 

Chemistry is traditionally divided into organic and inorganic chemistry. Formula: C12H3Fe, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 1271-51-8

Copper-Catalyzed Asymmetric Borylallylation of Vinyl Arenes

A copper-catalyzed, enantioselective method for the borylallylation of vinyl arenes is reported. The reaction produces enantioenriched and functionalized organoboron compounds by sequentially incorporating boryl and allyl groups onto the C – C bond of vinyl arenes. Copper-catalyzed borylative coupling of vinyl arenes with allyl phosphates successfully proceeds in a regio- and enantioselective manner in the absence of a palladium cocatalyst.

Copper-Catalyzed Asymmetric Borylallylation of Vinyl Arenes

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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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Immuno-Based Molecular Scaffolding of Glucose Dehydrogenase and Ferrocene Mediator on fd Viral Particles Yields Enhanced Bioelectrocatalysis

A virus-based nanostructuring strategy is proposed for improving the catalytic performance of integrated redox enzyme electrodes. Random arrays of adsorbed filamentous fd bacteriophage particles, used as scaffolds, are assembled onto gold electrode surfaces. The viral particles are endowed with functionally coupled enzymatic and redox properties, by the sequential immunological assembly of quinoprotein glucose dehydrogenase conjugated antibodies and ferrocene PEGylated antibodies on their protein shell. The resulting virus-scaffolded enzyme/redox mediator integrated system displays a large enhancement in the catalytic current generated per enzyme molecule (i.e., in enzymatic turnover) as compared with nonscaffolded integrated glucose oxidizing enzyme electrodes. The mechanism underlying the observed scaffolding-induced catalytic enhancement is deciphered. Confinement of the mediator on the viral scaffold enables fast electron transport rate and shifts the enzyme behavior into its most effective cooperative kinetic mode.

Immuno-Based Molecular Scaffolding of Glucose Dehydrogenase and Ferrocene Mediator on fd Viral Particles Yields Enhanced Bioelectrocatalysis

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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

 

Electric Literature of 1273-86-5, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1273-86-5, Name is Ferrocenemethanol, molecular formula is C11H3FeO. In a Article£¬once mentioned of 1273-86-5

mu-MIP: Molecularly Imprinted Polymer-Modified Microelectrodes for the Ultrasensitive Quantification of GenX (HFPO-DA) in River Water

Per- and polyfluoroalkyl substances (PFAS) are emerging as a hazardous class of environmental micropollutant, and robust, sensitive, and inexpensive sensing modalities are needed to detect the earliest onset of contamination of surface water. Here, we present a molecularly imprinted polymer (MIP)-modified microelectrode (r = 6.25 mum) sensor for the quantification of a pervasive environmental PFAS, GenX (HFPO-DA), in surface water obtained from the Haw River in North Carolina. A 20 nm film of o-phenylenediamine was electropolymerized in the presence of GenX to generate a templated polymer adjacent to the electrode surface with subsequent solvent extraction resulting in GenX-specific recognition sites. The oxidation of ferrocene methanol was observed as a function of GenX concentration, and the current decreased linearly with the concentration of GenX. A linear dynamic range of 1-5000 pM with a limit of detection of 250 fM and excellent selectivity against environmental interferents, such as humic acid and perfluorooctanesulfonate, was achieved. The use of oxygen reduction as an additional ambient detection mechanism and the amenability of microelectrodes to relatively resistive environmental matrices are demonstrated to extend the applicability of MIP-modified microelectrodes to environmental waterways as deployable sensors.

mu-MIP: Molecularly Imprinted Polymer-Modified Microelectrodes for the Ultrasensitive Quantification of GenX (HFPO-DA) in River 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