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This paper describes the preparation of a variety of 1?-substituted iodoferrocenes from 1-iodo-1?-(tri-n-butyltin)ferrocene by an electrophilic substitution of the tri-n-butyltin moiety with functionalized acylium and benzoylium species. Additionally, we demonstrate a Heck coupling protocol for these functionalized iodoferrocenes with ethenylferrocene.

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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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Ferrocene-terminated oligo(phenylenevinylene) (OPV) methyl thiols have been prepared by orthogonal coupling of phenylene monomers. Ethoxy substituents on the phenyl rings improve the solubility of OPV, enabling the synthesis of longer oligomers. Self-assembled monolayers containing a mixture of a ferrocene OPV methyl thiol and a diluent alkanethiol were deposited on gold. A cyclic voltammetric study of monolayers containing oligomers of the same length with and without ethoxy solubilizing groups reveals that both solubilized and unsolubilized oligomers form well-packed self-assembled monolayers. Changing the position of the solubilizing groups on an oligomer chain does not preclude packing of the oligomer in the monolayer. Conventional chronoamperometry, which can be used to measure rate constants up to ?104 S-1, is too slow to measure the electron-transfer rate through these oligomers over distances up to 35 A. OPV bridges are expected to be highly conjugated unlike oligo(phenyleneethynylene) bridges, which may be only partially conjugated because of rotation of the phenyl rings about the ethynylene bonds. Because of its high conjugation, OPV may prove useful as a molecular wire.

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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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Cyclotriphosphazenes with the general structure N3P3(OPh)5NH(CH2)3SiMe2OEt react with lithium aluminum hydride in diethyl ether to produce N3P3(OPh)5NH(CH2)3SiMe2H. Subsequent reaction of this species with alkenes in the presence of a platinum catalyst produced new cyclotriphosphazenes bearing alkoxy, siloxy, glycidyl, and ferrocenyl side groups. The yields depended on the type of catalyst and olefin used. Tetramethyl-1,3-divinyldisiloxane-platinum complex (DVDS:Pt) was a more efficient hydrosilylation catalyst than hydrogen hexachloroplatinic acid (CPA). Use of the latter catalyst yielded the silanol N3P3(OPh)deltaNH(CH2)3SiMe2OH, as a side product. This derivative subsequently condensed to produce a ring-linked phosphazene species. The hydrosilylation products were studied by 31P, 1H, and 13C NMR and infrared spectroscopy, elemental analysis, and mass spectrometry. Analogous reactions were investigated with the high-polymeric counterparts. Polymers with the general structure [NPRL8(NH(CH2)3SiMe2OEt)0.2]n, where R is -OCH2CF3 or -OC6H5, were synthesized and allowed to react with LiAlH4. The reduction process induced significant molecular weight decline from phosphorus-nitrogen bond cleavage, which was probably initiated by coordination of the aluminum to the nitrogen atoms in the polymer backbone and the amino side group. The influence of complexing agents, such as 4-(dimethylamino)pyridine and Et3N, on the reduction reactions was investigated.

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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 alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling.

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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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1,1,1-Trichloro-3-ethoxy-3-ferrocenylpropane (1a) gives ethynyl ferrocenyl ketone (2a) via an unusual elimination of hydrogen chloride, when 1a is treated with alkali and then acid.The ruthenium analog (1b) also affords ethynyl ruthenocenyl ketone (2b).No migration of the side chain is involved in this process.

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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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[(2-Ferrocenylvinyl)methyl]dimethylamine (2) was obtained in good yields and with perfect regio- and stereoselectivity by reaction of dimethylmethylideneammonium salts with vinylferrocene. After methylation of amine 2, [(2-ferrocenylvinyl)methyl]trimethylammonium iodide (4) was obtained in high yields and used to transfer the ferrocene-containing allyl group to various amines. By controlling reaction conditions, various linear and branched ferrocenyl-substituted allylamines could be obtained with good yields and selectivities. When anilines were used as substrates against ammonium salt 4, compounds originating from Friedel?Crafts reactions were also obtained, with complete regioselectivity towards the para position.

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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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New, thermally stable dipolar ferrocene-diketopyrrolopyrrole (Fc-DPP) dyads with alkene as a linker exhibited structure dependent first hyperpolarizabilities, betaHRS, recorded by a femtosecond HRS technique using a femtosecond (120 fs) pulsed laser light system at 900 nm at ambient temperature. On the basis of linear optical, electrochemical and TD-DFT studies, a good structure-polarization relationship has been established to account for the observed trends in first hyperpolarizabilities. The dyads exhibited fluctuating but matching solvatochromism. Nonlinear optical properties are modulated both by the strength of the acceptor as well as the length and nature of the pi-conjugation bridge. betaHRS of the dyads were compared with structurally related dyads in which the DPP core and the Fc donor are linked via an alkyne bridge. It is interesting to observe that the replacement of an alkyne link with alkene in these D-pi-A chromophores does not necessarily furnish enhanced betaHRS.

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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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The iron 2p and carbon 1s near-edge X-ray absorption fine structure (NEXAFS) spectra of substituted ferrocene compounds (Fe(Cp-(CH3) 5)2, Fe(Cp)(Cp-COOH), Fe(Cp-COOH)2, and Fe(Cp-COCH3)2) are reported and are interpreted with the aid of extended Hiickel molecular orbital (EHMO) theory and density functional theory (DFT). Significant substituent effects are observed in both the Fe 2p and C 1s NEXAFS spectra. These effects can be related to the electron donating/withdrawing properties of the cyclopentadienyl ligands and their substituents as well as the presence of pi* conjugation between the cyclopentadienyl ligand and unsaturated substituents.

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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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The enantioselective assembly of quaternary stereocenters through sequential functionalization of versatile carbon-atom precursors has the potential to systematize the synthesis of these ubiquitous stereogenic elements. Herein, we report two catalytic processes that allow the realization of this concept in the enantioselective synthesis of cyclopropanes. We demonstrate that C-H functionalization, carbene-transfer, and decarboxylative cross-coupling can sequentially take place in the same carbon atom to obtain highly enantioenriched cyclopropane products. The reactions reported herein give access to redox-active analogues of privileged aryldiazoacetates and demonstrate their enantioselective carbene transfer with a simple and practical rhodium catalyst.

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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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The application of ethynylferrocene, FcCCH (1), as a highly efficient electroactive precursor for the thiol-yne click reaction is presented. For this purpose, a wide range of functionalized thiols, namely 2-mercaptoethanol, 1-thioglycerol, 3-mercaptopropionic acid, 4-aminothiophenol, and benzene-1,3-dithiol as well as tetrathiol pentaerythritol tetrakis(3-mercaptopropionate), were investigated. This facile thiol-ethynylferrocene radical reaction has resulted in the quantitative formation and isolation of the newly ferrocenyl-vinyl sulfides FcCH=CHS(CH2)2OH (2Z and 2E), FcCH=CHSCH2CH(OH)CH2OH (3Z and 3E), FcCH=CHS(CH2)2COOH (4Z and 4E), FcC(CH2)S(1,4-C6H4)NH2 (5alpha), FcCH=CHS(1,3-C6H4)SCH=CHFc (6), and [FcCH=CHS(CH2)2COOCH2]4C (7). Thiol-ethynylferrocene reactions have been initiated either by heat, in toluene with AIBN, or by UV light irradiation in THF in the presence of DMPA as photoinitiator. The outcome of the hydrothiolation of ethynylferrocene strongly depends on the thiol structure and on the initiation method employed. A simple mixing of metallocene 1 with the thiol HS(CH2)2OH or HS(CH2)2COOH in a proper ratio, in THF at 20 C, in a initiator-free thiol-yne reaction, causes hydrothiolation of 1 to occur, allowing for the formation of vinyl sulfides 2Z, 2E and 4Z, 4E in good isolated yields. In contrast to the bis-addition typically observed for thiol-yne reactions, no double hydrothiolation to FcCCH has been observed for any of the thiols under any conditions studied. Electrochemical studies showed that tetrametallic compound 7, containing four sulfur-bridged ferrocenyl-vinyl moieties, behaves as a tetrapodal adsorbate molecule, exhibiting excellent chemisorption properties, and spontaneously forms robustly adsorbed 7 films onto Au or Pt electrode surfaces.

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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