Category: 1271-51-8

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A Trifluoromethylcarbene Source

The trifluoromethylcarbene (:CHCF3) was found to be conveniently generated from (2,2,2-trifluoroethyl)diphenyl-sulfonium triflate (Ph2S+CH2CF3 -OTf), which was successfully applied in Fe-catalyzed cyclopropanation of olefins, giving the corresponding trifluoromethylated cyclopropanes in high yields.

A Trifluoromethylcarbene Source

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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, electronic and photophysical characterization of pi-conjugated meso-ferrocenyl-porphyrin fluorescent redox switches

A series of meso-ferrocenyl-porphyrin dyads linked by four different pi-conjugated bridging units (directly bound, vinyl, ethynyl, and phenyl) have been synthesized to investigate the influence of the conjugated linker on both the electronic and photochemical properties of the porphyrin chromophore. The basic structure consists of 5-(Fc)-15-(4-methylbenzoate)-10,20-diphenylporphyrin zinc(II), where Fc = ferrocene, vinylferrocene, ethynylferrocene, or phenylferrocene. Upon introduction of the various electron-donating ferrocenyl moieties at the meso-position of the porphyrin ring, Soret and Q-band electronic transitions of the resultant dyads are red-shifted compared with those of the nonferrocenyl reference porphyrin system 15-(4-methylbenzoate)-10,20-diphenylporphyrin zinc(II). The electronic properties of these systems have been investigated by electrochemical (cyclic voltammetry) and computational (DFT/TDDFT) methods, while UV/vis absorption and fluorescence emission spectroscopic analysis is also presented. Collectively, electronic and photophysical analysis indicate a strong electronic communication between the porphyrin macrocycle and directly bound ferrocenyl, vinylferrocenyl, and ethynylferrocenyl dyads. The presence of a phenyl spacer acts to inhibit such electronic communication due to the orthogonal geometry of the bridging phenyl ring at the meso-position of the porphyrin macrocycle. In addition to electronic factors, and in particular for the directly bound 5-(ferrocenyl)-15-(4-methylbenzoate)-10,20-diphenylporphyrin zinc(II) dyad, computational analysis suggests that a significant ruffling of the porphyrin macrocyle from planarity is required to facilitate the bulky ferrocene group directly at the meso-position. Of particular note for each of the meso-ferrocenyl-porphyrin dyads is how fluorescence emission derived from the porphyrin S1 (pi-pi) excited state is quantitatively quenched due to photoinduced charge-transfer from the ferrocene unit onto the excited state porphyrin. Spectroelectrochemical studies demonstrate redox off/on switching of the porphyrin fluorescence emission via ferricenium/ferrocene redox cycling. Interestingly, it was found that the S0 ? S1 fluorescence emission is also switched-on following titration with the metal ions Ce(IV), Cu(II), and Fe(III) in acetonitrile.

Synthesis, electronic and photophysical characterization of pi-conjugated meso-ferrocenyl-porphyrin fluorescent redox switches

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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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Diels-Alder route to norbornane derived vicinal phosphane/borane frustrated Lewis pairs for the metal-free catalytic hydrogenation of alpha, beta-unsaturated ketones

The [4+2] cycloaddition reaction of the (dimesitylphosphino)cyclopentadienes 5a,b with N-phenylmaleimide gave the norbornene derivative 9. Its reduction with LiAlH4 produced the N-phenylpyrrolidino-annulated system 10. Treatment with Piers’ borane gave the respective P/B FLP 12 as the major product, which cleaved dihydrogen under mild conditions to yield the phosphonium/hydrido borate product 14. Reaction of the phosphino-norbornene 10 with 2 M equiv. of Piers? borane [HB(C6F5)2] followed by exposure to dihydrogen eventually gave the HB(C6F5)2 adduct 15. This served as a catalyst for the hydrogenation of a series of chalcone derivatives. The system requires a pre-activation period before becoming active for the conjugated enone hydrogenation.

Diels-Alder route to norbornane derived vicinal phosphane/borane frustrated Lewis pairs for the metal-free catalytic hydrogenation of alpha, beta-unsaturated ketones

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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

 

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Formula: C12H3Fe, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 1271-51-8, Name is Vinylferrocene, molecular formula is C12H3Fe

Ferrocenyl oligo(phenylene-vinylene) thiols for the construction of self-assembled monolayers

A short and efficient preparation of conjugated oligo(phenylene-ethylene) thiols bearing redox-active ferrocene moieties is described. While minimising the number of synthetic steps, the proposed strategy permits the development of sets of oligomers with varying chain length. The redox properties of the compounds in solution are determined. Preliminary studies of self-assembled monolayers (SAMs) on gold electrodes are discussed, and indicate that electron transfer through the SAMs is indeed rapid. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Ferrocenyl oligo(phenylene-vinylene) thiols for the construction of self-assembled monolayers

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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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Ferrocenyl-naphthalimide donor-acceptor dyads with aromatic spacer groups

The preparation and characterization of a series of dyads containing ferrocene donor and naphthalimide acceptor units, separated by aromatic spacer groups, are reported. The compounds contain a ferrocene-ethenyl spacer component linked to the 4-position of a naphthalimide by an ethynyl bridge, Fc-CH=CH-spacer-C?C-naphthalimide (Fc = ferrocenyl), where the spacers are 1,4-phenyl, 4,4?-biphenyl, and 9,10-anthryl. Precursors to the dyad systems, halo-spacer-C?C-naphthalimide, are also characterized where the halo-spacers are 1-bromophenyl, 4-bromobiphenyl, and 9-iodoanthryl. Various synthetic strategies are examined, with attachment of the spacer to 4-ethynylnaphthalimide followed by reaction with ethenylferrocene proving the most effective route. Crystal structures of the donor-spacer-acceptor (D-S-A) compound (E)-1-ethenylferrocenyl-4-(4-ethynyl-N-methyl-1,8-naphthalimide)benzene (7) and the precursor compounds (E)-4-bromo-4?-(ethenylferrocenyl) biphenyl (2) and 4-ethynyl-4?-(4-ethynyl-N-methyl-1,8-naphthalimide) biphenyl (4) are reported, with packing in the two naphthalimide derivatives dominated by offset pi-stacking interactions. Compounds containing the ferrocenyl groups show the anticipated one-electron oxidation processes at potentials that vary little with the spacer groups. Both the ferrocenyl derivatives and their naphthalimide precursors show reversible reduction waves. The single wave for the phenyl and biphenyl compounds and their precursors is assigned to reversible one-electron reduction of the naphthalimide unit. The corresponding anthracene derivatives display two reversible reductions associated with the naphthalimide and the anthryl moieties, respectively.

Ferrocenyl-naphthalimide donor-acceptor dyads with aromatic spacer groups

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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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Facile synthesis of first generation ferrocene dendrimers by a convergent approach using ditopic conjugated dendrons

A facile synthesis of new conjugated ferrocenyl-based dendrimers is reported and the compounds obtained have been fully characterized. The synthetic method consists of a two-step procedure, which combines olefination by the Wittig procedure and Pd-mediated C-C coupling, leading to high yields of first generation dendrimers with 3, 6 and 12 peripheral ferrocene units. The crystal structure of the conjugated ditopic ferrocenyl dendron and its aldehyde precursor are also described.

Facile synthesis of first generation ferrocene dendrimers by a convergent approach using ditopic conjugated dendrons

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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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PSiP-pincer type palladium-catalyzed dehydrogenative borylation of alkenes and 1,3-Dienes

Dehydrogenative borylation of alkenes and 1,3-dienes was realized by carrying out the reaction in the presence of bis(pinacolato)diboron (B2pin2) and a catalytic amount of PSiP-pincer palladium complex. This protocol has the following notable features. 1) Monoanionic nature of the PSiP-pincer ligand prevents the formation of boryl(hydrido)- or dihydridopalladium species, enabling synthesis of various vinyl- or dienylboronic esters in good yield from a 1:1 mixture of B2pin2 and alkenes or 1,3-dienes without forming hydroboration or hydrogenation products. 2) Due to the strong trans influence of the silicon atom, PSiP-pincer palladium complex showed high activity toward migratory insertion. 3) Suppression of these side-reactions and the high reactivity of the PSiP-pincer palladium complex enabled an efficient, successive dehydrogenative borylation to give 1,1- or 1,2-diborylated products depending on the kind of substituent on alkenes by using more than 2 equivalents of B2pin 2. Mechanistic study revealed that PSiP-pincer borylpalladium complex was generated from hydridopalladium complex and B2pin2, and this complex underwent alkene insertion followed by beta;- hydride elimination to give alkenylboronic ester with regeneration of the hydridopalladium complex.

PSiP-pincer type palladium-catalyzed dehydrogenative borylation of alkenes and 1,3-Dienes

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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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Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes

A visible-light-induced copper-catalyzed intermolecular hydroamination of alkenes using commercially accessible primary and secondary amines has been established. This effective method exhibits good tolerance of a broad range of functional groups and provides a facile access to an array of valuable amines with Markovnikov regioselectivity. The process can be positively expected to be used in bioactive amines, and it may provide new potential in the discovery of copper-catalyzed hydrofunctionalization reactions.

Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes

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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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Redox Activity of Vinylferrocene Copolymers by Electron Hopping Reaction in the Absence of Fluid Solvents

A series of novel copolymers consisting of a redox monomer, vinylferrocene, and an ion-conducting monomer, omega-methacryloyl-alpha-methoxy-oligo(ethylene oxide) (average molecular weight = 470), have been prepared by radical copolymerization and characterized.Ionic conductivity and redox activity of the copolymers, complexed with lithium perchlorate, have been explored by using complex impedance spectroscopy and solid state voltammetry with microelectrodes, respectively.The copolymer/salt complexes exhibit ionic conductivity of 1E-5 S cm-1 at room temperature and chemically reversible redox activity by themselves without any fluid solvents.The redox activity can be assigned to redox reactions of ferrocene sites in the bulk polymeric phases.The redox reactions are caused by propagation of oxidized (reduced) sites, generated at the electrode/copolymer interface, by electron transfer (electron hopping) reactions between mixed valent ferrocene/ferrocenium sites in the diffusion layer.Apparent electron diffusion coefficient for the electron transfer reactions, evaluated by potential step chronoamperometry, increases with increasing vinylferrocene composition in the copolymers.These copolymer/salt complexes are intrinsic redox conductors which exhibit appreciable ionic conductivity and redox activity by themselves without any fluid solvents and can be distinguished from conventional redox polymers.

Redox Activity of Vinylferrocene Copolymers by Electron Hopping Reaction in the Absence of Fluid Solvents

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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 Microchemical Diode with Submicron Contact Spacing Based on the Connection of Two Microelectrodes Using Dissimilar Redox Polymers

Closely spaced 0.2-1 num, Au microelectrodes (50 num long, 1-2 num wide, and 0.1 num thick) on Si3N4 can be functionalized with poly (viniylferrocene), PVFc +/0, or with an N,N’-dibenzyl-4,4′-bipyridinium-based polymer, (BPQ2+/+)n’ derived from hydrolysis of N,N’-bis<(p-trimethoxysilyl)benzyl>-4,4′-bipyridinium (I).Two- or eight-microelectrode arrays have been functionalized with PVFc+/0 or (BPQ2+/+)n.Adjacent microelectrodes can be connected with either polymer in the sense that net current can pass from one microelectrode to another, through the polymer,when one electrode is held at a potential where the polymer is oxidized and the other electrode is held at a potential where the polymer is reduced.From such steady-state current an estimate of the diffusion coefficient for charge transport, DCT, in the polymer can be made; values in the range 10-9 – 10-10 cm2/s are found and accord well with earlier measurements of DCT for the polymers studied.A two-terminal diode can be fabricated by coating one electrode with (BPQ2+/+)n and an adjacent electrode with PVFc+/0 such that there is a connection between the microelectrodes via the (BPQ2+/+)n/PVFc+/0 contact.Current passes when the applied potential is such that the negative lead is attached to the (BPQ2+/+)n-coated electrode and the positive lead is attached to the PVFc+/0-coated electrode.When the applied potential approaches the difference in the Eo’s of the two polymers, current flows with the crucial feature being a downhill (by ca. 0.9 V) cross redox at the (BPQ2+/+)n/PVFc+/0) interface, BPQ+ + Fc+ –> BPQ2+ +Fc0.Current does not flow between the microelectrodes when the applied is in the opposite sense, because the reaction BPQ2+ + Fco –> BPQ+ + Fc+ is uphill by ca. 0.9 V.The switching time of a microelectrochemical diode is controlled by the time required to oxidize and reduce the polymers.

A Microchemical Diode with Submicron Contact Spacing Based on the Connection of Two Microelectrodes Using Dissimilar Redox Polymers

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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