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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.

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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 reaction of FcCH2OH with chlorophosphates gave ferrocenyl phosphates FcCH2OP(O)(OR)2 [Fc = Fe(eta5-C5H5)(eta4-C5H4)], which readily separate into phosphate anions and ferrocenyl carbo-cations. The latter species undergoes consecutive reactions, for example, electrophilic aromatic substitutions. When nitriles, instead of alcohols, are treated with FcLi or tBuLi and chlorophosphates, chiral-pool based ferrocenylimino phosphoramidates Fc-CR=N-P(O)(OR*)2 are formed, which are promising candidates for anionic homo phospho-Fries rearrangements. Moreover, the sterically demanding chiral chlorophosphate with R* enabled oxidative couplings of the imines to form a diferrocenylazine. Similarly, the reaction of Fc?Li with 9-anthrylnitrile produced a 10-ferrocenyl-substituted product, contrary to a reaction at the C?N functionality. A planar-chiral ortho-P(S)Ph2-functionalized ferrocenylmethanol also gave carbo-cations under acidic conditions. These species can be sulfurized in a unique way giving thio ethers, whereby the in situ formed 1,2-P(S)Ph2,CH2+ ferrocene cation acts as the sulfur and electron source. However, lowering the substrate concentration prevents sulfur migration, resulting in electrophilic substitution reactions with aromatic solvents. Planar-chiral ferrocenylmethyl thio or anisyl derivatives were applied as ligands in Pd-catalyzed Suzuki?Miyaura C,C cross-couplings for the atroposelective synthesis of hindered biaryls with up to 26 % ee at low catalyst loadings (1 mol-% Pd).

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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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As potential nonlinear optical materials, 12-nitro-4,7-bis(2-ferrocenylvinyl)[2.2]paracyclophane (1) and 12-nitro-4,5,7,8-tetrakis(2-ferrocenylvinyl)[2.2]paracyclophane (2) have been synthesized by Pd-catalyzed coupling reactions of vinylferro-cene with the precursor cyclophanes 9 and 13, respectively. The absorption and electrochemical properties of 1 and 2 are also described. VCH Verlagsgesellschaft mbH.

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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 catalytic addition reactions of ferrocenyl ketones with terminal olefins in the presence of Ru(H)2(CO)(PPh3)3 as catalyst have been studied. Benzoylferrocene reacts with triethoxyvinylsilane, styrene and vinylferrocene, respectively, to give 1:1 coupling products I-III in high yields. C-H bond cleavage takes place at the carbon atom of the benzene ring at the ortho position of the carbonyl group and C-C bond formation takes place at the terminal carbon atom of the olefins. 2-Furoylferrocene reacts with vinylferrocene to give a 1:1 coupling product IV and the C-H bond cleavage takes place at the carbon atom of the furan ring at the ortho position of the carbonyl group and the C-C bond formation takes place at the terminal carbon atom of vinylferrocene. The new products I-IV have been characterized by elemental analysis, 1H-NMR and MS. The X-ray crystal structure of IV has been determined.

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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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Complex cyclic azomethine imines possessing a beta-aminocarbonyl motif can be accessed readily from simple alkenes and hydrazones. This alkene aminocarbonylation approach allows formation of ketone-derived azomethine imines of unprecedented complexity. Since unsymmetrical hydrazones are used, two stereoisomers are formed: the reactivity of chiral derivatives is explored in both intra- and intermolecular systems.

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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

Chemical engineers ensure the efficiency and safety of chemical processes, adapt the chemical make-up of products to meet environmental or economic needs, and apply new technologies to improve existing processes. Related Products of 1271-51-8. Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. Introducing a new discovery about 1271-51-8, Name is Vinylferrocene

Photoinduced electron transfer processes of two newly synthesized tetrads with a triphenylamine (TPA) as central building block, to which bisfullerenes (C60) and bisferrocenes (Fc) are covalently connected, have been studied. One of them has a TPA linked with one C60 moiety and two ferrocene moieties C60-TPA-(Fc)2 and another tetrad has a TPA linked with two C60 moieties and one ferrocene unit (C60)2-TPA-Fc. The photophysical properties of (C60)m-TPA-(Fc)n have been investigated by applying the picosecond time-resolved fluorescence and nanosecond transient absorption techniques in both polar and nonpolar solvents. The charge separation process via the excited singlet state of the C60 moiety of the C60-TPA-(Fc)2 is more efficient than that of the (C60)2-TPA-Fc. It is found that the ratio of Fc-donor to C60-acceptor affects charge separation efficiency via the excited singlet state of the C60 moiety.

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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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Promoters are ubiquitous in industrial heterogeneous catalysts. The wider roles of promoters in accelerating catalysis and/or controlling selectivity are, however, not well understood. A model system has been developed where a heterobimetallic active site comprising an active metal (Rh) and a promoter ion (Ga) is preassembled and delivered onto a metal-organic framework (MOF) support, NU-1000. The Rh-Ga sites in NU-1000 selectively catalyze the hydrogenation of acyclic alkynes to E-alkenes. The overall stereoselectivity is complementary to the well-known Lindlar’s catalyst, which generates Z-alkenes. The role of the Ga in promoting this unusual selectivity is evidenced by the lack of semihydrogenation selectivity when Ga is absent and only Rh is present in the active site.

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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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Cyclic azomethine imines possessing a beta-aminocarbonyl motif are accessed from simple alkene and hydrazone starting materials. A thermal, concerted alkene aminocarbonylation pathway involving an imino-isocyanate intermediate is proposed and supported by DFT calculations. A notable feature of the process is the steric shielding present in the dipoles formed, which allows for facile purification of the products by chromatography or crystallization. In addition, a fluorenone-derived reagent is reported, which provides reactivity with several alkene classes and allows for mild derivatization of the dipoles into beta-aminoamides, beta-aminoesters, and beta-amino acids.

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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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o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane-functionalized molecules. Using 1-Li-2-OTf-o-C2B10H10 as a precursor, o-carboryne undergoes an efficient [2 + 2] cycloaddition with a large variety of vinyl ethers at room temperature to give a series of carborane-fused cyclobutanes in very good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope ranging from alkyl- to aryl- and to silyl-substituted vinyl ethers. A stepwise reaction mechanism is proposed based on the control experiments, which is supported by DFT calculations. All new compounds have been fully characterized by 1H, 13C, and 11B NMR spectroscopy as well as HRMS spectrometry. Some are further confirmed by single-crystal X-ray analyses.

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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 1,3-dithiol-2-one derivatives via [4 + 2] Diels-Alder cycloaddition reaction of 4,5-bis(dibromomethyl)-1,3-dithiol-2-one with vinyl-substituted compounds have been synthesized. Structures of all the newly synthesized compounds are well supported by spectral data such as 1H-NMR, MS, and elemental analysis. The structures of IVf and IVg have been analyzed by X-ray crystallography.

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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