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The new types of ferrocenyloxaaliphatic acid ester, FcCHROCHR?COOMe (R = H, Me, Ph; R? = H, Me) (7) have been prepared by the action of alkoxides derived from methyl glycolate or methyl lactate on the corresponding ferrocenylcarbinyl acetates (2) or N,N,N-trimethylferrocylammonium iodides (4). The esters obtained were accompanied by a small quantity of oligomeric esters, FcCHR(OCHR?CO)nOMe (9), and with more or less ferrocyl methyl ethers (8). As opposed to the alkaline hydrolysis of the analogous methyl benzoxyacetate (6) into benzoxyacetic acid (5) the acidification of sodium alkanoates 10 obtained by saponification of esters 7 gave unexpectedly the corresponding ferrocenylcarbinols 1. In a similar way the esters 7 were converted into mixtures of the mentioned carbinols and diferrocyl ethers 11 under action of aqueous hydrochloric acid. The mechanisms of the reactions 10 ? 1 and 7 ? 1, 11 are discussed.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A mixture of cis/trans isomers of phospha[1]ferrocenophanes equipped with one iPr group at the alpha position to the bridging PhP moiety was prepared. Both isomers (cis-4 and trans-4) were obtained as racemates and could be separated so that their thermal properties were investigated individually. The molecular structure of cis-4 was determined by single-crystal X-ray analysis showing a tilt angle alpha=26.35(8). Interconversion between both isomers occurred in the melt at elevated temperatures and revealed that the trans isomer is thermodynamically more stable. Structural and thermodynamic data was complemented by DFT calculations (B3PW91/6-311+G(d,p) and B3PW91-D3(BJ)/6-311+G(d,p)). Performance of thermal ring-opening polymerization (ROP) of trans-4 at 230 C gave polymers and cyclic oligomers. Gel permeation chromatography (GPC) of the sulfurized polymer resulted in a molecular weight of 62.5 kDa (Mw) and a polydispersity index of 1.39 (PDI). Mass spectrometric analysis of the oligomers showed the presence of cyclic species from dimers to heptamers. After sulfurization, preparative thin layer chromatography led to the separation of three isomeric dimers. Structural characterization of these dimers by single-crystal X-ray analysis led to the conclusion that the Fe?Cp bond breaks during the thermal ROP process. A mechanism similar to the known mechanism of the photolytic ROP of ferrocenophanes is proposed.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A functionalized magnetic nanoparticle including an organometallic sandwich compound and a magnetic metal oxide. The functionalized magnetic nanoparticle may be reacted with a metal precursor to form a catalyst for various C?C bond forming reactions. The catalyst may be recovered with ease by attracting the catalyst with a magnet.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A cationic rhodium-sparteine complex, [((-)-sparteine)Rh(eta4- COD)]+ (1+; COD = 1,5-cyclooctadiene) was obtained, isolated as its tetrafluoroborate salt (1BF4), and characterized using X-ray crystallography and multinuclear (1H, 13C) NMR spectroscopy. This is the first structurally characterized sparteine complex of rhodium. The Rh-N bonds are unusually long (2.214(3) and 2.242(3) A), apparently due to steric repulsion between COD and sparteine. 1H NMR exchange experiments (EXSY) demonstrate a dynamic process that results in an overall 180 rotation of the COD methine protons in solution (CD 2Cl2) with a first-order rate constant of 460 s -1 at the coalescence temperature (314 K) and interpolated rate constant of 150 s-1 at 298 K. Temperature-dependent NMR studies yield DeltaH? = 13.0 ± 0.3 kcal mol-1, DeltaS? = -5 ± 1 cal mol-1 K-1, such that DeltaG?298 = 14.3 ± 0.3 kcal mol-1. DFT studies (B3LYP) indicate that the loosely bound (-)-sparteine ligand rotates through a pseudo-tetrahedral transition state where both ligands are rotated approximately 90 relative to each other. While both ligands remain bound (eta4-COD, kappa2-sparteine), bonding to sparteine is weakened much more than bonding to COD in the transition state. DFT computed DeltaG?298 and DeltaS? values (15.55 kcal mol -1 and -2.67 cal mol-1 K-1, respectively) agree very well with the experimental values. Attempts to find alternative mechanisms involving partial dechelation of COD and (-)-sparteine yielded slightly higher barriers along with positive DeltaS values for intermediate formation.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Computed Properties of C14H19FeN, The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 31886-57-4, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine,introducing its new discovery.

Circular dichroism spectra of the optically active (R)- and (S)-enantiomers of N,N-(dimethylamino)ethylferrocene (Ugi´s amine) were studied for a free form and for their diastereomeric salts with ? l(+)-tartaric acid.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Density functional calculations reveal that, whereas the reaction of 2-propyl-N,N-diisopropylbenzamide (6) with tBuLi in the presence of potentially tridentate donor ligands may result in lateral deprotonation of 6, the behavior of the Lewis base is non-trivial. The ability of N and O donor centers in the co-solvent to resist Li+ coordination is found to be synonymous with interaction of lithium with the formally deprotonated carbanion center. Low-energy structures have been identified whose predicted 1H and 13C NMR spectroscopic shifts are in excellent agreement with experiment. Reaction of 2-isopropyl-N,N-diisopropylbenzamide (5) with tBuLi in the presence of bidentate Lewis base N,N,N?,N?- tetramethylethylenediamine (TMEDA) yields material that is suggested by NMR spectroscopy to be laterally deprotonated and to have the formulation 5-Li laTMEDA. In spite of the tertiary aliphatic group at the 2-position in 5, X-ray crystallography reveals that the crystalline material isolated from the treatment of 5/(-)-sparteine with tBuLi is a lateral lithiate in which amide coordination and solvation by bidentate Lewis base results in the Li + ion interacting with the deprotonated alpha-C of the 2-iPr group (2.483(8) A). The tertiary carbanion center remains essentially flat and the adjacent aromatic system is highly distorted. The use of a chiral co-solvent results in two diastereomeric conformers, and their direct observation in solution suggests that interconversion is slow on the NMR timescale. Two’s company, three’s a crowd: Tridentate ligands promote tertiary carbanion formation through benzylic deprotonation. New calculations suggest that the ligands can adopt variable denticities in solution. The alternative use of bidentate ligands N,N,N?,N?-tetramethylethylenediamine and (-)-sparteine is now shown to promote benzylic reaction, accompanied by the retention of carbanion-lithium bonding (see figure). Copyright

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A new method for the determination of enantiomeric composition of N,N-dimetriyl-alpha-ferrocenylethylamine by 1H NMR spectroscopy using (S)-mandelic acid as a chiral protonating agent was proposed.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A molecular mechanics force field has been developed for the conformational analysis of amido- and aalpha-aminoferrocenes. Parameterization for ring-substituent rotational barriers in amidoferrocenes and other cross-conjugated derivatives have been calculated using DFT on both the free and complexed cyclopentadienyl ligand. Modeled structures of (diisopropylamido)- and (dimethylamido)ferrocene and N,N-dimethyl-alpha-ferrocenylethylamine are in agreement with those determined through single-crystal X-ray diffraction. The diastereo-selective lithiation of N,N-dimethylferrocenylethylamine and sparteine-mediated enantio-selective lithiation of (diisopropylamido)ferrocene using MeLi have been modeled through an assumed reversible adduct formation at the amine nitrogen or amide oxygen, followed by an irreversible ring lithiation. Results indicate that selectivity results from ring lithiation via the adduct conformer with the shortest C-Hring- – -H3C-Li interaction.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Classical synthetic approach to highly enantiomeric-enriched ferrocenes relies on the formation of their conjugates with (R,R)-tartaric acid. Herein, the quantum chemical calculations based on X-ray data as an initial approximation, were carried out for both (R)- and (S)-diastereomers of N,N-(dimethyl-1-ferrocenyl)ethylamine (Ugi’s amine) with (R,R)-tartaric acid. A high correlation between the experimental data and the calculated Gibbs free energies values of solvation was obtained. Based on the advanced DFT calculations, the chemical aspects of the separation of the diastereomeric complexes of (R)- and (S)-FcCH(CH3)N(CH3)2 with (R,R)-tartaric acid were clarified. Quantum chemical calculations made it possible to justify the use of methanol as a solvent in the successful separation of the diastereomeric complexes of the Ugi’s amine. This mathematical approach can be used in practice to separate racemates of other bioactive ferrocene compounds, for example, ferrocenyl alkyl azoles.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Reaction of [IrCp?Cl2]2 with ferrocenylimines (Fc=NAr, Ar=Ph, p-MeOC6H4) results in ferrocene C-H activation and the diastereoselective synthesis of half-sandwich iridacycles of relative configuration Sp?,RIr?. Extension to (S)-2-ferrocenyl-4-(1-methylethyl)oxazoline gave highly diastereoselective control over the new elements of planar chirality and metal-based pseudo-tetrahedral chirality, to give both neutral and cationic half-sandwich iridacycles of absolute configuration Sc,Sp,RIr. Substitution reactions proceed with retention of configuration, with the planar chirality controlling the metal-centred chirality through an iron-iridium interaction in the coordinatively unsaturated cationic intermediate.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis