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[3]Dendralene and [4]dendralene are converted smoothly into tricarbonyliron complexes. The structures of four complexes analyzed by DFT and single-crystal X-ray analysis show that, in contrast to free hydrocarbons, complexed dendralenes prefer a roughly in-plane conformation. The complexes are stable towards Fe(CO)3 group migration up to 150 C. The synthetic value of Fe(CO)3 complexation in the dendralene series is demonstrated through a variety of selective synthetic manipulations (Diels-Alder reaction, dipolar cycloaddition, Simmons-Smith cyclopropanation, dihydroxylation, olefin cross metathesis) that are not achievable by direct transformation of the free hydrocarbons. Application to the synthesis of a previously unreported, highly reactive linear/cross-conjugated hydrocarbon is also described. Simplicity through complexation: Tricarbonyliron complexes of dendralenes are readily prepared and stable. They allow the formation of products that cannot be accessed directly from dendralenes, including unprecedented structures (see scheme).

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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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We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl beta-nitroalkenes, this reagent provides unparalleled access to beta-nitrohydrins and beta-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.

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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 series of mono- and multimeric polyamine-containing ferrocenyl complexes containing a quinoline motif were prepared. The complexes were characterised by standard techniques. The molecular structure of the monomeric salicylaldimine derivative was elucidated using single crystal X-ray diffraction and was consistent with the proposed structure. The antiplasmodial activity of the compounds were evaluated in vitro against both the NF54 (chloroquine-sensitive) and K1 (chloroquine-resistant) strains of Plasmodium falciparum. The polyamine derivatives exhibit good resistance index values suggesting that these systems are beneficial in overcoming the resistance experienced by chloroquine. Mechanistic studies suggest that haemozoin formation may be the target of these quinoline complexes in the parasite. Some of the complexes exhibit moderate to high cytotoxicity against WHCO1 oesophageal cancer cells in vitro. The monomeric ferrocenyl-amine complexes exhibit potent activity against this particular cell line. The complexes were also screened against the G3 strain of Trichomonas vaginalis and the salicylaldimine complexes demonstrated promising activity at the tested concentration. All of these compounds show no inhibitory effect on several common normal flora bacteria, indicative of their selectivity for eukaryotic pathogens and cancer.

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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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Polysiloxane-encapsulated “Pd”-nanoclusters were generated by reduction of Pd(OAc)2 with polymethylhydrosiloxane, which functions as a reducing agent as well as a capping material for production and stabilization of catalytically active “Pd”-nanoparticles. Chemoselective hydrogenation of functional conjugated alkenes was achieved by in-situ- or ex-situ-generated polysiloxane-stabilized “Pd”- nanoclusters under mild reaction conditions in high yields. Electron microscopy, UV-vis, and NMR studies of the reaction mixture during the catalytic transformation were performed and, in conjunction with catalyst poisoning experiments, demonstrated unequivocally the role of polysiloxane-encapsulated “Pd”-nanoclusters as the real catalytic species. The recyclability of the “Pd”-nanoclusters was established by reusing the solid left after the reaction.

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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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By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.

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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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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.

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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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Attempted catalytic hydroboration of (4-methoxyphenyl)ethene 1 with R,R-3-isopropyl-4-methyl-5-phenyl-1,3,2-oxazaborolidine 6 proceeded extremely slowly relative to the 3-methyl analog 2 derived from phi-ephedrine when diphosphinerhodium complexes were employed. With phosphine-free rhodium catalysts, especially the 4-methoxy-phenylethene complex 7, the reaction proceeded rapidly and quantitatively to give only the corresponding (E)-vinylborane 9 and 4-methoxyethylbenzene 8 in equimolar amounts. Isotopic labeling and kinetic studies demonstrated that this reaction pathway is initiated by the formation of a rhodium hydride with subsequent reversible and regiospecific H-transfer to the terminal carbon, giving an intermediate which adds the borane and then eliminates the hydrocarbon product. Further migration of the secondary borane fragment from rhodium to the beta-carbon of the coordinated olefin occurs, followed by Rh-H beta-elimination which produces the vinylborane product and regenerates the initial catalytic species. When the same catalytic reaction is carried out employing catecholborane in place of the oxazaborolidine, an exceedingly rapid turnover occurs. The products are again 4-methoxyethylbenzene and the (E)-vinylborane 23 but accompanied by the primary borane 24 in proportions which vary with the experimental conditions. None of the secondary borane, which is the exclusive product when pure ClRh(PPh3)3 is employed as catalyst, is formed. The product variation as a function of initial reactant concentration was fitted to a model in which the rhodium-borane intermediate in the catalytic cycle undergoes two competing reactions-beta-elimination of Rh-H versus addition of a further molecule of catecholborane. The model demonstrates that a kinetic isotope effect of 3.4 operates in the beta-elimination step, but none is evident in the addition of catecholborane B-D to rhodium. A similar analysis was successfully applied to the catalytic hydrosilylation of 4-methoxystyrene, with HSiEt3, again employing the phosphine-free rhodium catalyst 7; the product distribution between primary silane 29 and vinylsilane 28 was successfully predicted. The results intimate that silation (i.e., the formation of vinylsilanes under the conditions of catalytic hydrosilylation) can best be explained by a Rh-H based mechanistic model rather than the commonly assumed variant on the Chalk-Harrod catalytic cycle. They provide an explanation for the “oxygen effect” on the rate of Rh-catalyzed hydrosilylations.

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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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An efficient procedure for the enantioselective synthesis of beta-ferrocenyl-beta-amino alcohols, a new class of central chiral ferrocene derivatives suitable for the elaboration of auxiliaries and ligands for asymmetric synthesis, is described. Key steps of the method are the catalytic asymmetric dihydroxylation of 1-ferrocenyl alkenes and the regio- and stereoselective azide substitution of the hydroxyl group adjacent to the ferrocene moiety. The stereochemistry of the substitution step has been established by X-ray diffraction analysis of a cyclic derivative. The first catalytic enantioselective synthesis of a beta-ferrocenyl-beta-amino acid derivative is also disclosed.

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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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Disclosed are a metallocenyl dendrimer, an organic memory device using the metallocenyl dendrimer and a method for fabricating the organic memory device. The metallocenyl dendrimer may be composed of a dendrimer and metallocenes as redox species linked to the dendrimer. The organic memory device may possess the advantages of shorter switching time, decreased operating voltage, decreased fabrication costs and increased reliability. Based on these advantages, the organic memory device may be used as a highly integrated, large-capacity memory device.

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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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Both ferrocenethiol and ferrocene-1,1′-dithiol, Fe(C5H5)(C5H4SH) and Fe(C5H4SH)2, add to activated olefins to give 1:1 and 1:2 adducts, respectively.The base-catalysed (NEt3) reactions of the monofunctional ferrocenethiol with the mono-olefins methyl methacrylate, methyl vinyl sulfone and benzylidene acetone lead to expected 1:1 adducts whereas 2:1 adducts are obtained with bifunctional olefins such as divinyl sulfone and dibenzylidene acetone.The corresponding bifunctional ferrocene-1,1′-dithiol gives 1:2 adducts with methyl methacrylate, methyl vinyl ketone and benzylidene acetone.For comparison, the aliphatic 2-ferrocenyl-ethanethiol, Fe(C5H5)(C5H4-CH2CH2SH), was reacted with methyl vinyl sulfone and divinyl sulfone.In all cases, the disulfides Fc-SS-Fc and Fc-CH2CH2-SS-CH2CH2-Fc, respectively, are also formed.The acid-catalysed (HCl) reactions of ferrocenethiol and ferrocene-1,1′-dithiol, Fe(C5H5)(C5H4SH) and Fe(C5H4SH)2, with isobutyl vinyl ether produce the expected 1:1 and 1:2 adducts although the formation of dimercaptals is also possible.Thus the reaction of ferrocene-1,1′-dithiol with isobutyl vinyl ether leads to both the 1:2 adduct and the 2-methyl 1,3-dithia-<3>ferrocenophane, Fe(C5H4S)2CH(CH3), and the HCl-catalysed addition of ferrocenethiol to 1,4-butadienol divinyl ether gives 1,1-di(ferrocenylmercapto) ethane, CH3CH(SFc)2.The new sulfur derivatives of ferrocene were characterized by 1H and 13C NMR spectroscopy.Keywords: Iron; Ferrocene; Ferrocene thiol; Addition to olefins; NMR

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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