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Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone “co-factors” by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an “electron hole” will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species.

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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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[Problem] measuring telomerase activity of the compounds. [Solution] type I (R1 The alkylene group of C1 a-6; R2 , R3 And R4 The alkyl group is C1 a-3; and n is 0 or 1 m is, at least one of 1) naphtha range imido derivative. [Drawing] no (by machine translation)

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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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Conjugated microporous polymers (CMPs) have full access to the organic synthesis toolbox and feature-rich functionality, structural diversity, and high surface area. We incorporated ferrocene (Fc) into the backbones of CMPs and systematically engineered their optical energy gaps. Compared with the CMPs without Fc units yet adopting a similar molecular orbital level, Fc-based CMPs can sufficiently generate reactive oxygen species (ROS) under visible light. The resultant ROS are able to effectively decompose the absorbed pollutants, including organic dyes and chemical warfare agents. Specifically, Fc-based CMPs significantly outperform commercial TiO2 (P25) in the degradation of methylene blue and are capable of converting 2-chloroethyl ethyl sulfide (a mustard gas simulant) into a completely nontoxic product.

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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 thiophene tungsten Fischer carbene complexes of type [(CO)5W=C(OMe)R] (1, R = 2-Th; 4, R = fcthFc) and [(CO)5W=C(OMe)-R?-(OMe)C=W(CO)5] (2, R? = th; 5, R? = fcthfc) was synthesized for investigating low energy charge transfer interactions between the carbene substituents and the transition metal carbonyl fragment incorporating the thiophene heterocyclic system (Th = Thienyl; th = 2,5-thiendiyl; Fc = ferrocenyl; fc = 1,1?-ferrocenediyl). Electrochemical investigations were carried out on these complexes to get a closer insight into the electronic properties of 1, 2, 4 and 5. Typical electrode reactions could be found for the carbene reductions itself and for the tungsten carbonyl oxidation processes in all metal carbene complexes. However, for the thiophene complex 2 two well-separated one-electron reduction events were observed, suggesting an interaction of the Fischer carbene moieties in 2-, over the thiophene bridge. Reversible one-electron redox events for the ferrocenyl moieties in complexes 4 and 5 were also observed. During the UV-Vis-NIR spectroelectrochemical investigations typical low energy absorptions for the mixed-valent alpha,alpha?-diferrocenyl thiophene increment were found for these two complexes, as well as high energy NIR absorptions, which were attributed to metal-metal charge transfer transition between the tungsten carbonyl increment and the ferrocenyl units (complexes 4 and 5). Further infrared spectroelectrochemical studies reveal that the electronic interactions between the tungsten carbene and the ferrocenyl electrophores in the corresponding cationic species (4+, 42+, 5+, 52+) can be described with weakly coupled class II systems according to Robin and Day.

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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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In (1?-benzoylferrocenyl)diphenylmethanol, [(PhCO-C5H4)Fe(C5H4)]CPh 2OH (C30H24FeO2), there is an intramolecular O-H…O hydrogen bond with O…O 2.891 (2) A; the ferrocenyl unit adopts an eclipsed conformation and the molecules are linked into centrosymmetric dimers by C-H…O hydrogen bonds with C…O 3.357 (3) A, to generate a cyclic R44(16) motif.

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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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Two homologous ferrocene phosphanylcarboxylic acids, viz., 1?-[(diphenylphosphanyl)methyl]ferrocene-1-carboxylic acid (HL1) and [1?-(diphenylphosphanyl)ferrocenyl]acetic acid (HL2), were synthesized and studied as ligands in PdII complexes. The addition of these hybrid donors to [PdCl2(MeCN)2] led to the bis-phosphane complexes trans-[PdCl2(HL1-kappaP)2] and trans-[PdCl2(HL2-kappaP)2]. In contrast, the reactions of HL1 and HL2 with the PdII acetylacetonate (acac) complexes [(LYC)Pd(acac)], where LYC = 2-[(dimethylamino-kappaN)methyl]phenyl-kappaC1 (LNC) and 2-[(methylthio-kappaS)methyl]phenyl-kappaC1 (LSC), proceeded under proton transfer and replacement of the acac ligand, giving rise to O,P-bridged phosphanylcarboxylate dimers [LYCPd(mu(P,O)-L1)]2 and molecular chelates [LYCPd(L2-kappa2O,P)]2, respectively. The analogous reactions involving 1?-(diphenylphosphanyl)-1-ferrocenecarboxylic acid (Hdpf) provided the macrocyclic tetramer [LNCPd(mu(P,O)-dpf)]4 and the dimer [LSCPd(mu(P,O)-dpf)]2. The reactions of HL1 with [Pd(acac)2] only led to an ill-defined, insoluble material, whereas those with HL2 produced a separable mixture of the bis-chelate complexes trans-[Pd(L2-kappa2O,P)2], cis-[Pd(L2-kappa2O,P)2], and [Pd(acac)(L2-kappa2O,P)].

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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 and flexible asymmetric synthesis of planar chiral 2-mono- and 2,2?-disubstituted 1,1?-bisbenzoylferrocenes 4 and 6 is reported. Key step is a highly diastereoselective ortho-metalation of 1,1?-bisbenzoylferrocene 1 via the corresponding bis-SAMP-hydrazone 2 (de?96%), followed by trapping with various carbon, silicon, phosphorus and sulfur electrophiles. Cleavage of the monosubstituted hydrazones 3 led to monosubstituted ketones 4 (ee?98%). Further ortho-substitution of the hydrazones 3 afforded 2,2?-disubstituted hydrazones 5, which could be cleaved to disubstituted ferrocenyl diketones 6 (ee?99%). The new methodology allows a broad and flexible fine-tuning of ferrocenyl ligands desired in asymmetric catalysis. Ozonolysis or reductive hydrazone cleavage using TiCl3 or SnCl2 were the methods of choice to remove the auxiliary.

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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 new potentially C3-symmetric phosphine ligand ‘manphos’ has been obtained and fully characterized. The ligand which is a tri-ferrocenyl-tetra-phosphine is obtained in a simple and effective two step synthesis starting from 1,1?-dibromoferrocene via the intermediate compound tris-(1?-bromoferrocenyl)phosphine or alternatively via 1′-bromo-1-diphenylphosphinoferrocene. The iso -propylphosphino-analogue of manphos, tris-(1′-diisopropylphosphinoferrocenenyl)phosphine, has also been obtained, in addition to several functionalised derivatives of triferrocenylphosphine where the ferrocene rings have been substituted in the 1?-position.

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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 system for the catalytic redox isomerization of the allylic alcohol 1-octen-3-ol to 3-octanone is presented. The homogeneous ruthenium(II) catalyst contains a monodentate phosphane ligand with a ferrocene moiety in the backbone and provides 3-octanone in quantitative yields. The activity is increased by nearly 90 % with respect to the corresponding triphenyl phosphane ruthenium(II) complex. By grafting the catalyst at the surface of a dendrimer, the catalytic activity is further increased. By introducing different spacers between ferrocene and phosphorus, the influence on the electronic properties of the complexes is shown by evaluating the electrochemical behavior of the compounds.

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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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Gold(i) phosphine complexes are often used in catalysis, but the role of their auxiliary ligands still remains poorly understood. Thus, building on our previous research, we prepared a series of Au(i) complexes [Au2(mu-R2PfcCN)2][SbF6]2 (fc = ferrocene-1,1?-diyl) to assess the effect of phosphine groups PR2 on the catalytic properties of these highly catalytically active, dimeric compounds. Catalytic testing in Au-mediated cyclisation of N-propargyl amides to 2-substituted 5-methyleneoxazolines showed that weaker donating phosphines gave rise to more active, albeit partly destabilised, catalysts. Nevertheless, thanks to their self-stabilisation by reversible nitrile coordination, [Au2(mu-R2PfcCN)2]+ cations readily converted into catalytically active species (by dissociation) and, in addition, remained catalytically active even at very low metal loadings. The experimental results were supported by the trends in 1JPSe coupling constants for R2P(Se)fcCN as a measure of ligand basicity, and by DFT calculations.

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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