Category: 31886-57-4

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Ferrocene compounds XXIII. Synthesis and reactions of the new type of methyl ferrocyloxyalkanoates

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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Rhodium-Catalyzed Asymmetric Allylation of Malononitriles as Masked Acyl Cyanide with Allenes: Efficient Access to beta,gamma-Unsaturated Carbonyls

A rhodium-catalyzed regio- and enantioselective intermolecular allylation of malononitriles as masked acyl cyanides (MAC) with terminal and symmetrical internal allenes is reported. A RhI/Josiphos catalytic system combined with subsequent oxidative degradation of the primary adducts enables a straightforward access to alpha-branched, beta,gamma-unsaturated carbonyl compounds. The present protocol exhibits perfect atom economy in the allylation step and is characterized by a great functional group compatibility. Furthermore, the use of alpha-substituted malononitriles allowed for the construction of all-carbon quaternary centers.

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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

Application of 31886-57-4, In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum. 31886-57-4, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine, molecular formula is C14H19FeN. In a Article，once mentioned of 31886-57-4

Synthesis of derivatives of (alpha-(dimethylamino)ethyl)ferrocene via lithiation reactions and the structure of 2-(alpha-(dimethylamino)ethyl)-1,1?,3-tris(trimethylsilyl)ferrocene

Dilithiation of Fe(C5H4CHMeNMe2)(C5H5) (1) with BuLi is predominantly homoannular but with BuLi/TMED is heteroannular. Heteroannular dilithiation predominates in the reaction of BuLi/TMED with Fe(C5H3(CHMeNMe2)SiMe3-1,2)(C 5H5), Fe(C5H3(CHMeNMe2)SiMe 3-1,2)(C5H4SiMe3), and Fe(C5H2(CHMeNMe2) (SiMe3)2-1,2,3,)(C5H4SiMe 3) (11). The lithioferrocenes react with ClSiMe3 to afford isolable products although some mixtures of isomers are difficult to characterize. The [3]ferrocenophane Fe(C5H3(CHMeNMe2)S3-1,2,3)(C 5H4) is obtained from 1 as are [Fe(C5H5)(C5H3(CHMeNMe 2)-1,2)]xQ (x = 2, Q = PPh; x = 1, Q = SMe; x = 1, Q = PPhCMe3 (only one diastereomer because of strong chiral induction)) and Fe(C5H4CHMeNMe2)(C5H 4AsPh2). Crystals of 11 are monoclinic: a = 17.800 (2) A, b = 11.760 (1) A, c = 13.931 (2) A, beta = 107.142 (5), Z = 4, space group P21/n. The structure was solved by conventional heavy-atom methods and was refined by full-matrix least-squares procedures to R = 0.054 and Rw = 0.061 for 2745 reflections with I ? 3sigma(I).

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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 (S)-1 – ferrocene ethyl dimethylamine preparation process (by machine translation)

The invention discloses a (S)- 1 – ferrocene ethyl dimethylamine preparation process. In the preparation process, in order to acetyl ferrocene as raw materials, the use of metal Ir complex with a chiral ferrocenyl tridentate ligands L* The reaction complex as a catalyst, by asymmetric catalytic hydrogenation to obtain (S)- 1 – ferrocenyl ethanol, then acetylation, dimethylamine substituted reaction, to obtain (S)- 1 – ferrocene ethyl dimethylamine. With the traditional chiral separating method preparation (S)- 1 – ferrocene ethyl dimethylamine processes of the prior art, the invention has the advantages embodied in: mild reaction conditions, the operation is simple, stereoselectivity is good, high yield, production cycle is short, the amount “three wastes”, easy industrialization, having great value and social and economic benefits. (by machine translation)

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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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Heterolytic cleavage of dihydrogen by frustrated Lewis Pairs derived from alpha-(dimesitylphosphino)ferrocenes and B(C6F5) 3

Treatment of the alpha-dimethylamino[3]ferrocenophane system 3 with methyl iodide followed by dimesitylphosphine (Mes2PH) gave the alpha-(dimesitylphosphino)[3]ferrocenophane 5. This forms a frustrated Lewis pair [5/8] with B(C6F5)3 (8) that rapidly reacts with dihydrogen under ambient conditions to probably give the phosphonium cation/hydrido borate anion salt [5-H+/H-8-]. This, however, is unstable under the applied reaction conditions with regard to replacement of the newly formed phosphonium leaving group at the ferrocenophane a-position for hydride from the [HB(C6F5)3 -] counteranion to eventually yield the unfunctionalized [3]ferrocenophane product (10) and Mes2PH· B(C 6F5)3 (11) – both characterized by independent syntheses. Analogously, Ugi’s amine (6) was converted to (1-(dimesitylphosphino) -ethyl)ferrocene (7). The frustrated pair [7/8] consumes dihydrogen under similar conditions to yield the reduction products ethylferrocene (14) and Mes2PH · B(C6F5)3 (11).

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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

In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. name: (S)-N,N-Dimethyl-1-ferrocenylethylamine, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine, belongs to chiral-nitrogen-ligands compound, is a common compound. name: (S)-N,N-Dimethyl-1-ferrocenylethylamineCatalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article, authors is Zagorevskii, D. V., once mentioned the new application about name: (S)-N,N-Dimethyl-1-ferrocenylethylamine.

MASS SPECTROMETRY OF ?-COMPLEXES OF TRANSITION METALS XX. DIMETHYLAMINOALKYL DERIVATIVES OF FERROCENE AND CYMANTRENE; THE DETERMINATION OF THE DISTRIBUTION AND THE TOTAL CONTENT OF DEUTERIUM LABEL

The mass spectrometry behaviour of dimethylaminomethyl- and alpha-(dimethyl-amino)ethyl derivatives of cymantrene and ferrocene, their iodine methylates as well as of the deutero analogues of these compounds has been studied.It has been shown that mass spectrometry can be successfully employed for the quantitative determination of the total deuterium content in aminoalkyl derivatives of cymantrene and ferrocene, the distribution of the label between the dimethylaminoalkyl group and the metallocenyl fragment and in case of the dimethylaminomethylferrocene also between thesubstituted and unsubstituted cyclopentadienyl rings.The data on the distribution of the isotopic label were used to ascertain the mechanism of fragmentation of the dimethylaminomethylferrocene under electron impact.

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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

In homogeneous catalysis, catalysts are in the same phase as the reactants. Chemistry is traditionally divided into organic and inorganic chemistry. Safety of (S)-N,N-Dimethyl-1-ferrocenylethylamine, Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article，Which mentioned a new discovery about 31886-57-4

Optically Active Transition-Metal Complexes. 9.1 A General Stereoselective Route to alpha-Chiral (A)-Tricarbonyl(eta6-ethylbenzene)chromium Complexes. Novel Organometallic Phosphine Catalysts for the Asymmetric Hydrovinylation Reaction

Treatment of (R)-[{alpha-(dimethylamino)ethyl}-eta6-benzene]Cr(CO)3 with esters of chloroformic acid leads to stereoselective substitution of the dimethylamino group for a chloro substituent. The reaction can be extended to systems in which the chromium arene complex, after metalation, is diastereoselectively substituted in the ortho position with carbon and silicon electrophiles to generate planar chirality. The chloro group in turn can be replaced stereoselectively for various phosphorus, nitrogen, and oxygen nucleophiles. Both substitution reactions in the benzylic position proceed via retention of configuration. The addition of cyanide is not stereospecific. The phosphine derivatives are efficient catalysts for the enantioselective hydrovinylation of styrene to 3-phenyl-1-butene. X-ray crystal structures establish the absolute configuration of (R)-[(alpha-chloroethyl)eta6-benzene]Cr(CO)3, (R)-[{alpha-(diphenylphosphanyl)ethyl}-alpha6-benzene]Cr(CO) 3, and (pS,S)-[l-(alpha-cyanoethyl)-2-methyl-eta6-benzene]Cr(CO) 3.

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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

Synthetic Route of 31886-57-4, In some cases, the catalyzed mechanism may include additional steps. Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. 31886-57-4, Name is (S)-N,N-Dimethyl-1-ferrocenylethylamine,introducing its new discovery.

Substituted ferrrocenecarboxylic acids and esters

The synthesis of Fe(eta-C5H5)(eta-C5H3(CHMeNMe2)(COOH)-1,2), 3a, and its methyl and ethyl esters is described.Esterification of 3a by using RI in DMA affords Fe(eta-C5H5)(eta-C5H3(CHMeOH)(COOR)-1,2), R = Me, Et, with retention of configuration at the chiral center.The variable temperature 1H NMR spectrum of 3a reveals H-bonding between the two functional groups.

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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

Irreversible inhibitors are therefore the equivalent of poisons in heterogeneous catalysis.SDS of cas: 31886-57-4, Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme and thus slowing or preventing a reaction from occurring. 31886-57-4, name is (S)-N,N-Dimethyl-1-ferrocenylethylamine. In an article，Which mentioned a new discovery about 31886-57-4

Enantiopure Ferrocene-Based Planar-Chiral Iridacycles: Stereospecific Control of Iridium-Centred Chirality

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

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PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES

The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.

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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