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Isomeric phosphinoferrocene ligands, viz. 1?-(diphenylphosphino)-1-cyanoferrocene (1) and 1?-(diphenylphosphino)-1-isocyanoferrocene (2), show markedly different coordination behaviours. For instance, the reactions of 1 with [PdCl2(MeCN)2] and [(LNC)Pd(mu-Cl)]2 (LNC = [2-(dimethylamino-kappaN)methyl]phenyl-kappaC1) produced the ?phosphine? complexes [PdCl2(1-kappaP)2] (7) and [(LNC)PdCl(1-kappaP)] (8), and the latter was converted into the coordination polymer [(LNC)Pd(mu(P,N)-1)][SbF6] (9). Conversely, the reaction of 2 with [(LNC)Pd(mu-Cl)]2 involved coordination of the phosphine moiety and simultaneous insertion of the isocyanide group into the Pd-C bond, giving rise to the P,eta1-imidoyl complex [PdCl(Ph2PfcN?CC6H4CH2NMe2-kappa3C,N,P)] (10; fc = ferrocene-1,1?-diyl). Compound 10 was further transformed into the Fischer carbene [PdCl(Ph2PfcN(Me)CC6H4CH2NMe2-kappa3P,C,N)][BF4] (11) by methylation with [Me3O][BF4]. The reactions of 2 with Pd-Me and Pd(eta3-allyl) precursors also led to imidoyl complexes [Pd(mu-Cl)(Ph2PfcN?CR-kappa2C,P)]2 (R = Me: 12, R = allyl: 15), which were cleaved with PPh3 into the corresponding monopalladium complexes [PdCl(PPh3)(Ph2PfcN?CR-kappa2C,P)] (R = Me: 13, R = allyl: 16). The treatment of 12 and 15 with thallium(i) acetylacetonate (acac) produced [Pd(acac-O,O?)(Ph2PfcN?CR-kappa2C,P)] (R = Me: 17, R = allyl: 18). Through proton transfer, these complexes reacted with Ph2PCH2CO2H, ultimately producing bis-chelate complexes [Pd(Ph2PCH2CO2-kappa2O,P)(Ph2PfcN?CR)] (R = Me: 19, R = prop-1-enyl (sic!): 20). In addition, compound 13 was converted into the P-chelated carbene [PdCl(PPh3)(Ph2PfcN(Me)CMe-kappa2C,P)][BF4] (14). Compounds 10, 11, 13 and 14 were studied by cyclic voltammetry and by DFT computations.

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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 general method for the preparation of ferrocenylamines involves the reactions of ferrocenyl bromide, FcBr*, with the sodium salt of an amine or amide in the presence of copper(I)bromide/pyridine.The syntheses of diferrocenylphenylamine and triferrocenylamine, NFc2Ph and NFc3, respectively, are reported, and the hydrolysis of N-ferrocenyl acetamide to give ferrocenylamine, NH2Fc, is described.The system of the ferrocenyl- and/or phenyl-substituted derivatives of ammonia, NFcnX3-n (n=0-3; X=H, Ph), is characterised on the basis of mass, UV VIS and in particular of 1H and 13C NMR spectroscopic data.

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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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Palladium catalyzed Negishi, Suzuki and Stille cross-coupling reactions of enantiopure 2,2?-diiodo-1,1?-binaphthyl with the corresponding 1,1?-dimetalloferrocenes gave the C2-symmetric binaphthyl bridged ferrocene 1-1,1?-(1,1?-binaphthyl-2,2?-diyl)ferrocene (1). The latter was obtained by Stille coupling with the bis(trimethylstannyl) derivative but not with the bis(tributylstannyl) one. Products of alkyl group transfer from tin to binaphthyl were obtained as the main products in both cases. The stereochemical result of these cross-coupling reactions in the positions 2 and 2? of 1,1?-binaphthyl depends on the reactivity of 1,1?-dimetalloferrocenes. Negishi coupling proceeds stereoconservatively (affording enantiopure product 1). Complete racemization of binaphthyl moiety occurs during the reactions with less reactive boron and tin organometallics. Proposed different reaction pathways include C1-symmetric palladium(II) intermediate in the former and configurationally unstable C2-symmetric pallada(IV)cyclic intermediate in the latter cases. In contrast to the cross-coupling reactions, free radical arylation of ferrocene with enantiopure 1,1?-binaphthyl-2,2?-bisdiazonium salt gave predominantly oligomeric binaphthyl bridged ferrocenes and only traces of the partially racemized product 1.

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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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For a series of ferrocenyl thiophenes of type Fe(eta5-C5H4-(4-R-cC4H2S-3-yl))(eta5-C5H4-(C6H3-3,5-(CF3)2) [R = H (3a), OMe (4a)], Fe(eta5-C5H4-(4-R-cC4H2S-3-yl)(eta5-C5H4-CHO) [R = H (3b), OMe (4b)], and Fe(eta5-C5H4-(4-R-cC4H2S-3-yl)(eta5-C5H4-C?N) [R = H (3c), OMe (4c)], the influence of electron-withdrawing substituents at the ferrocenyl moiety and electron-donating groups at the thiophene unit on the electronic behavior of 3a-c and 4a-c is reported. The coupling of the ferrocenyl and the thiophene moieties has been realized using the Negishi C,C cross-coupling reaction protocol. Compounds 3a and 4c were structurally characterized by single-crystal X-ray diffraction studies. In electrochemical measurements the ferrocenyl redox potential depends on the particular substitution at the ferrocenyl and the thiophene unit. Moreover, UV/Vis/NIR studies showed ligand-to-metal charge transfer (LMCT) interactions, which occur after oxidation and are shifted bathochromically as the donor-acceptor energy gap decreases. Using different substituents, possessing electron-withdrawing or donating capabilities, allows adjusting the energy difference between the ferrocenium-acceptor unit and the donating thiophene system.

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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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We report the synthesis and full characterization of the entire haloferrocene (FcX) and 1,1?-dihaloferrocene (fcX2) series (X = I, Br, Cl, F; Fc = ferrocenyl, fc = ferrocene-1,1?-diyl). Finalization of this simple, yet intriguing set of compounds has been delayed by synthetic challenges associated with the incorporation of fluorine substituents. Successful preparation of fluoroferrocene (FcF) and 1,1?-difluoroferrocene (fcF2) were ultimately achieved using reactions between the appropriate lithiated ferrocene species and N-fluorobenzenesulfonimide (NFSI). The crude reaction products, in addition to those resulting from analogous preparations of chloroferrocene (FcCl) and 1,1?-dichloroferrocene (fcCl2), were utilized as model systems to probe the limits of a previously reported “oxidative purification” methodology. From this investigation and careful solution voltammetry studies, we find that the fluorinated derivatives exhibit the lowest redox potentials of each of the FcX and fcX2 series. This counterintuitive result is discussed with reference to the spectroscopic, structural, and first-principles calculations of these and related materials.

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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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(Chemical Equation Presented) Chirality3: A new ferrocene-based diphosphine ligand is applied to the asymmetric hydrogenation of alpha-substituted cinnamic acids. The P-centered-, C-centered-, and planar-chiral ligand (RC,RC,SFc,S Fc,SP,SP)-1 displays unprecedented enantioselectivity in this Rh-catalyzed reaction (see scheme; cod = cycloocta-1,5-diene).

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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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Ligands of the formula (I) secondary phosphine-Q-P(=O)HR1 (I) in the form of mixtures of diastereomers or pure diastereomers, in which secondary phosphine is a secondary phosphine group with hydrocarbon radicals or heterohydrocarbon radicals as substituents; Q is a bivalent bisaryl or bisheteroaryl radical with an axial chiral centre to which the two phosphorus atoms are bonded in the ortho positions to the bisaryl or bisheteroaryl bridge bond, or Q is a bivalent ferrocenyl radical with a planar chiral centre or without a planar chiral centre, to which the phosphorus atom of the secondary phosphine is bonded directly or via a C1-C4-carbon chain to a cyclopentadienyl ring, the -P*(=O)HR1 group is bonded either on the same cyclopentadienyl ring in ortho position to the bonded secondary phosphine or on the other cyclopentadienyl ring; P* is a chiral phosphorus atom, and R1 is a hydrocarbon radical, a heterohydrocarbon radical or a ferrocenyl radical, where R1 is a ferrocenyl radical with a planar chiral centre when Q is a ferrocenyl radical without a planar chiral centre. Metal complexes of these ligands are homogeneous catalysts for asymmetric addition reactions, particularly hydrogenations.

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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 mononuclear non-heme manganese(V)-oxo complex, [MnV(O)(TAML)]- (1), was synthesized by activating dioxygen in the presence of olefins with weak allylic C-H bonds and characterized structurally and spectroscopically. In mechanistic studies, the formation rate of 1 was found to depend on the allylic C-H bond dissociation energies (BDEs) of olefins, and a kinetic isotope effect (KIE) value of 16 was obtained in the reactions of cyclohexene and cyclohexene-d10. These results suggest that a hydrogen atom abstraction from the allylic C-H bonds of olefins by a putative MnIV-superoxo species, which is formed by binding O2 by a high-spin (S = 2) [MnIII(TAML)]- complex, is the rate-determining step. A Mn(V)-oxo complex binding Sc3+ ion, [MnV(O)(TAML)]–(Sc3+) (2), was also synthesized in the reaction of 1 with Sc3+ ion and then characterized using various spectroscopic techniques. The binding site of the Sc3+ ion was proposed to be the TAML ligand, not the Mn-O moiety, probably due to the low basicity of the oxo group compared to the basicity of the amide carbonyl group in the TAML ligand. Reactivity studies of the Mn(V)-oxo intermediates, 1 and 2, in oxygen atom transfer and electron-transfer reactions revealed that the binding of Sc3+ ion at the TAML ligand of Mn(V)-oxo enhanced its oxidizing power with a positively shifted one-electron reduction potential (DeltaEred = 0.70 V). This study reports the first example of tuning the second coordination sphere of high-valent metal-oxo species by binding a redox-inactive metal ion at the supporting ligand site, thereby modulating their electron-transfer properties as well as their reactivities in oxidation reactions.

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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 phosphorus-chiral diphosphine 1,1?-bis(1-naphthylphenylphosphino)ferrocene (1a) and its new electronically modified derivatives 1b-d bearing methoxy and/or trifluoromethyl groups in para positions of the phenyl rings were investigated as ligands in rhodium-catalyzed (asymmetric) hydroformylation. Depending on ligand basicity, high-pressure NMR and IR characterization of the respective (diphosphine) rhodium dicarbonyl hydride precursor complexes revealed subtle differences in the occupation of bis-equatorial (ee) and equatorialapical (ea) coordination geometries. The high ee:ea ratio of the four complexes contrasted with the clear ea preference observed for the related achiral compound dppf (1,1?-bis-(diphenylphosphino)ferrocene). In the hydroformylation of styrene the best result (50% ee) was obtained by employing the best pi-acceptor ligand 1c, incorporating two p-trifluoromethyl substituents. Substrate electronic variations using 4-methoxystyrene and 4-chlorostyrene showed a pronounced influence on turnover frequencies, branched/linear aldehyde product ratios, and enantiodiscrimation, whereas in the hydroformylation of 1-octene ligand electronic perturbations did affect only the rate, but not the selectivity of the reaction.

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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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Synthetic approaches based on the direct borylation of ferrocene by BBr3, followed by boryl substituent modification, or on the lithiation of ferrocene derivatives and subsequent quenching with the electrophile FBMeS2, have given access to a range of ferrocene derivatized Lewis acids with which to conduct a systematic study of fluoride and cyanide binding. In particular, the effects of borane electrophilicity, net charge, and ancillary ligand electronics/cooperativity on the binding affinities for these anions have been probed by a combination of NMR, IR, mass spectrometric, electrochemical, crystallographic, and UV-vis titration measurements. In this respect, modifications made at the para position of the boron-bound aromatic substituents exert a relatively minor influence on the binding constants for both fluoride and cyanide, as do the electronic properties of peripheral substituents at the 1 ?- position (even for cationic groups). By contrast, the influence of a CH2NMe3 + substituent in the 2- position is found to be much more pronounced (by >3 orders of magnitude), reflecting, at least in part, the possibility in solution for an additional binding component utilizing the hydrogen bond donor capabilities of the methylene CH2 group. While none of the systems examined in the current study display any great differentiation between the binding of F- and CN- (and indeed some, such as FcBMeS2, bind both anions with equal affinity within experimental error), much weaker boronic ester Lewis acids will bind fluoride (but give a negative response for cyanide). Thus, by the incorporation of an irreversible redox-matched organic dye, a two-component [BMes2/B(OR)2] dosimeter system can be developed capable of colorimetrically signaling the presence of fluoride and cyanide in organic solution by Boolean AND/NOT logic.

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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