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The syntheses and characterization of heterodi- and heterotrimetallic complexes of general formulas [Pd{[(eta5-C5H 3)-C(R)=N-R?]Fe[(eta5-C5H 4)-C(R)=N-R?]}Cl(PPh3)] [Pd{[(eta5-C5H3)C(C6H 5)=N-C6H5]Fe[(eta5-C 5H4)-C(O)=N-C6H5]}Cl(PPh 3)], and [Pd2{Fe[(eta5-C5H3)-C(R)= N-R?]2}Cl2(PPh3)2] {with R = H, CH3, or C6H5 and R?= phenyl or benzyl groups} are reported. The X-ray crystal structure of the meso-form of [Pd2{Fe[(eta5-C5H3)-C(CH 3)=N-C6H5]2}Cl2(PPh 3)2] (2b) is also described.

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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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Conformational preferences for isolated molecules of ferrocene, 1-bromoferrocene and 1,1?-dibromoferrocene were obtained by combined use of matrix-isolation infrared spectroscopy and quantum chemical calculations. Monomeric ferrocene and 1-dibromoferrocene were found to exist in a low temperature argon matrix (T = 15 K) exclusively in the eclipsed configuration, which corresponds to their most stable conformation in gas phase. On the other hand, for the neat compounds in crystalline phase, intermolecular interactions induce conformational disorder, leading to presence in the room temperature polymorphic forms of monomeric units with the staggered (or nearly staggered) conformation. 1,1?-Dibromoferrocene exists in both gas phase and low temperature argon matrix in two conformers of C2 symmetry (C2-I and C2-II), with eclipsed cyclopentadienyl moieties and Br atoms opposed to H atoms. The populations of the two conformers trapped in the as-deposited matrix were found to correspond to those estimated from theory for the room temperature equilibrium gas phase. By increasing the temperature of the matrix (up to 35 K), the gas phase lower energy form (C2-I) converted to the C2-II form. Besides allowing the precise structural and spectroscopic characterization of the two forms, these studies also revealed that the C2-II conformer (having a largest dipole moment) is stabilized in the matrix media, thus becoming more stable than the C2-I form under these conditions. Very interestingly, the room temperature stable polymorph of the compound (Tfus = 325.4 ± 0.1 K) is composed by 1,1?-dibromoferrocene units exhibiting the C2v symmetry eclipsed conformation with opposed bromine atoms, which for the isolated molecule corresponds to the highest energy conformation along the ring torsional coordinate and is the transition state structure between the two symmetry equivalent C2-II minima. Differential scanning calorimetry, polarized light thermomicroscopy and infrared measurements on 1,1?-dibromoferrocene allowed to identify a new polymorph of the compound, with Tfus = 320.2 ± 0.1 K. On the whole, the results presented in this article represent illuminating examples of intermolecularly-induced conformational disorder in solid phase and of its relevance to polymorphism.

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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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Highly enantioselective kinetic resolution of racemic planar-chiral metallocenylphosphine sulfides was realized by the molybdenum-catalyzed asymmetric ring-closing metathesis reaction with the krel values of up to 147. The enantiomerically enriched 1,4-but-2-enylene-bridged ferrocenylphosphine sulfides thus obtained could be purified to enantiomerically pure forms by simple recrystallization from hot methanol, and subsequent reduction of the phosphine sulfides provided the corresponding planar-chiral phosphines with retention of the enantiomeric homogeneity. This is a rare example of preparing planar-chiral ferrocenylphosphines by catalytic asymmetric reactions. The single-enantiomer planar-chiral ferrocenylphosphines were applied as chiral ligands in the rhodium-catalyzed asymmetric 1,4-addition reaction (the Hayashi-Miyaura conjugate addition reaction) of phenylboronic acid to 2-cyclohexenone to show excellent enantioselectivity and high yields. The NMR studies clarified that the butenylene-bridged ferrocenylphosphine coordinated to a rhodium(I) cation in a monodentate fashion and an interaction of the bridging olefin moiety to the rhodium atom was not detected.

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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 Pd-catalyzed, asymmetric oxidative cross-coupling reaction between ferrocenes and heteroarenes is described. The process, which takes place via a twofold C-H bond activation pathway, proceeds with modest to high efficiencies (36-86%) and high levels of regio- and enantioselectivity (95-99% ee). In the reaction, air oxygen serves as a green oxidant and excess amounts of the coupling partners are not required. The process is the first example of a catalytic asymmetric biaryl coupling reaction that occurs via double C-H bond activation. Finally, the generated coupling products can be readily transformed into chiral ligands and catalysts.

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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 first ferrocene-fused organometallic compounds derived from the buckybowl sumanene (C21H12) are presented. Both compounds, sumanenylferrocene and 1,1?-disumanenylferrocene, have been synthesized by Negishi-type cross-coupling of iodosumanene and were studied crystallographically. Sumanenylferrocenes form unique packing motifs, which are both different from those of their corannulene congeners and sumanene itself.

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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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Kinetics of photoinduced electron transfer from a series of electron donors to the triplet excited states of a series of nonplanar porphyrins, hydrochloride salts of saddle-distorted dodecaphenylporphyrin ([H 4 DPP]Cl 2 ), tetrakis(2,4,6-trimethylphyenyl)porphyrin ([H 4 TMP]Cl 2 ), tetraphenylporphyrin ([H 4 TPP]Cl 2 ), and octaphenylporphyrin ([H 4 OPP]Cl 2), were investigated in comparison with those of a planar porphyrin, zinc [tetrakis(pentafluorophenyl)]porphyrin [Zn(F 20 TPP)(CH 3 CN)], in deaerated acetonitrile by laser flash photolysis. Theresulting data were evaluated in light of the Marcus theory of electron transfer, allowing us to determine reorganization energies of electron transfer to be 1.21 eV for [H 4 TMP]Cl 2 ,1.29 eV for [H 4 TPP]Cl 2 , 1.45 eV for [H 4 OPP]Cl 2 , 1.69 eV for [H 4 DPP]Cl 2 , and 0.84 eV for [Zn(F 20 TPP)(CH 3 CN)]. The reorganization energies exhibited a linear correlation relative to the out-of-plane displacements, which represent the degree of nonplanarity. The rate of electron-transfer reduction of diprotonated porphyrins is significantly slowed down byconformational distortions of the porphyrin ring. This indicates that t he reorganization energy of electron transfer is governed by structural change, giving a larger contribution of inner-sphere bond reorganizationenergy rather than outer-sphere solvent reorganization energy.

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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 stereoelectronic influence of phosphine substituents on the coordination and catalytic properties of phosphinoferrocene carboxamides was studied for the model compounds R2PfcCONHMe (1a-d), where fc = ferrocene-1,1?-diyl and R = i-Pr (a), t-Bu (b), cyclohexyl (Cy; c), Ph (d), using experimental and DFT-computed parameters. The electronic parameters were examined via 1JSeP coupling constants determined for R2P(Se)fcCONHMe (6a-d) and C?O stretching frequencies of the Rh(I) complexes trans-[RhCl(CO)(1-kappaP)2] (7a-d); the steric properties of 1a-d were assessed through Tolman?s ligand cone angles (theta) and solid angles (Omega). Generally, a very good agreement between the calculated and experimental values was observed. Whereas the donor ability of the amidophosphines was found to increase from 1d through 1a,c to 1b, the trends in steric demand suggested by the two parameters differed, reflecting the different spatial properties of the phosphine substituents. In situ NMR studies and catalytic tests on the Suzuki-Miyaura cross-coupling of 4-bromoanisole with a bicyclic 4-tolylborate to give 4-methyl-4?-methoxybiphenyl using [Pd(eta2:eta2-cod)(eta2-ma)] (cod = cycloocta-1,5-diene, ma = maleic anhydride) as a Pd(0) precursor revealed that different Pd-1 species (precatalysts) were formed from different ligands and participated in the reaction. Specifically, the bulky and electron-rich donor 1b favored the formation of [Pd(1b)(ma)], while the remaining ligands provided the corresponding bis-phosphine complexes [Pd(1)2(ma)]. The best results in terms of catalyst longevity and efficacy were observed for ligands 1a,c.

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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 synthesis and characterization of a series of carbosilane-supported ferrocenyl phosphine ruthenium complexes of type SiMe4-n(Fe(eta5-C5H4SiMe2(CH2)3)((eta5-C5H4PR2)RuCl2(eta6-p-cymene)))n (p-cymene = 1-i-Pr-4-Me-C6H4; n = 2: 10a, R = Ph; 10b, R = cC6H11; 10c, R = 2-(5-Me)C4H2O); n = 4: 11a, R = Ph; 11b, R = cC6H11; 11c, R = 2-(5-Me)C4H2O)) is described. For comparative reasons, the non-immobilized ferrocenyl phosphine ruthenium complexes [FcPR2(RuCl2(eta6-p-cymene))] (Fc = Fe(eta5-C5H4)(eta5-C5H5); 9a, R = Ph; 9b, R = cC6H11; 9c, R = 2-(5-Me)C4H2O) were prepared. The molecular structure of 9c in the solid state is reported confirming the expected tetrahedral coordination sphere about the phosphorus atom and the “piano-stool” geometry about ruthenium. The ruthenium complexes 9-11 are catalytically active in the addition of benzoic acid to propargyl alcohol to form beta-oxopropyl benzoate. The obtained activities and productivities show that a good solubility of the catalyst is necessary for a successful catalytic reaction. Furthermore, the rate of the reaction can be influenced by using less basic and electron-withdrawing phosphine ligands.

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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 1,1′-diheteroatom-substituted ferrocene derivatives as well as acylated ferrocenes was prepared efficiently by a unified strategy that consists of selective mono- and 1,1′-dilithiation reactions and subsequent coupling with carbon, phosphorus, sulfur and halogen electrophiles. Chemical oxidation of the ferrocene derivatives by benzoquinone, 2,3-dichloro-5,6- dicyanobenzoquinone, AgPF6, or 2,2,6,6-tetramethyl-1-oxopiperidinium hexafluorophosphate provided the corresponding ferrocenium salts. The redox potentials of the synthesized ferrocenes were determined by cyclic voltammetry, and it was observed that all new ferrocenium salts have stronger oxidizing properties than standard ferrocenium hexafluorophosphate. An initial application of selected derivatives in an oxidative bicyclization revealed that they mediate the transformation under considerably milder conditions than ferrocenium hexafluorophosphate. Quantum chemical calculations of the reduction potentials of the substituted ferrocenium ions were carried out by using a standard thermodynamic cycle that involved the gas-phase energetics and solvation energies of the contributing species. A remarkable agreement between theory and experiment was found: the mean average deviation amounted to only 0.030-V and the maximum deviation to 0.1-V. This enabled the analysis of various physical contributions to the computed reduction potentials of these ferrocene derivatives, thereby providing insight into their electronic structure and physicochemical properties. Copyright

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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 one-pot, four-component, copper-catalysed double-“click” functionalisation of a novel 1,1?-desymmetrised ferrocene backbone is reported. Using an array of alkynes and azides, a library of ferrocene compounds was developed, demonstrating the scope of this methodology for its potential application in the assembly of novel materials, ligands or biological sensors.

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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