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General Description

Chlorocarbonyl ferrocene is an organometallic compound consisting of a ferrocene core with a carbonyl group and a chlorine atom attached to the cyclopentadienyl rings. It is primarily used as a building block in the synthesis of other organometallic compounds and in the preparation of organometallic catalysts. Chlorocarbonyl ferrocene has been investigated for its potential use in catalytic reactions, particularly in the field of organic synthesis. It is a versatile compound with potential applications in the development of novel materials and in pharmaceutical research. However, it is important to handle chlorocarbonyl ferrocene with care, as it is a reactive and potentially hazardous chemical.

Check Digit Verification of cas no

The CAS Registry Mumber 1293-79-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,9 and 3 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1293-79:
(6*1)+(5*2)+(4*9)+(3*3)+(2*7)+(1*9)=84
84 % 10 = 4
So 1293-79-4 is a valid CAS Registry Number.

1293-79-4 Well-known Company Product Price

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  • (91032)  Ferrocenoyl chloride  for HPLC derivatization, ≥96.0% (AT)

  • 1293-79-4

  • 91032-1G

  • 4,639.05CNY

  • Detail

1293-79-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Ferrocenoyl chloride

1.2 Other means of identification

Product number -
Other names chloro(cyclopenta-2,4-dien-1-ylidene)methanolate,cyclopenta-1,3-diene,iron(2+)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1293-79-4 SDS

1293-79-4Relevant articles and documents

1,2-DISUBSTITUIERTE FERROCENE VIA 2-FERROCENYL-2-OXAZOLINE

Schmitt, Guenter,Klein, Peter,Ebertz, Wolfgang

, p. 63 - 72 (1982)

2-Ferrocenyl-2-oxazolines, available from the reaction of chlorocarbonylferrocene with aziridines and subsequent acid-catalyzed isomerisation, are metallated (lithiated) regiospecifically in the 2-position of the ferrocenyl moiety.Further reaction of the metallated compounds with electrophiles gives 1,2-disubstituted ferrocenes solely.In contrast to the analogous 2-phenyl-2-oxazolines, 2-ferrocenyl-2-oxazolines exhibit high stability under acid-catalyzed solvolytic attack conditions.The reason for this unexpected behaviour is discussed.

Palladium-Catalyzed C-H Functionalization of Ferrocenecarboxylic Acid by using 8-Aminoquinoline as a Removable Directing Group

Sattar, Moh.,Praveen,Durga Prasad, Ch.,Verma, Ajay,Kumar, Shailesh,Kumar, Sangit

, p. 240 - 253 (2016)

A mild and efficient palladium-catalyzed synthetic method for the C-H functionalization of N-(quinolin-8-yl)ferrocenecarboxamide has been developed. Various aryl iodides containing I, NO2, CN, COMe, CO2Et, and NH functionalities and also alkyl iodides underwent the Pd-catalyzed intermolecular carbon-carbon bond forming reaction with ferrocenecarboxamide successfully which led to a diverse array of bis(aryl/alkyl)ferrocenecarboxamides in 34-92% yields. Cross-coupling of the ferrocenyl C-H bond with aryl iodides can also be achieved utilizing an economical Ni catalyst. Additionally, selective monoalkylation of ferrocenecarboxamide was studied using sodium bicarbonate as base and dibenzylphosphoric acid as additive under Pd-catalyzed reaction conditions. Subsequently, removal of the directing group, 8-aminoquinoline, from bis(aryl)ferrocenecarboxamides led to bis(aryl)ferrocenes bearing versatile methyl ester and carboxaldehyde functional groups.

Functionalized ferrocenes: The role of the para substituent on the phenoxy pendant group

Vera, José L.,Rullán, Jorge,Santos, Natasha,Jiménez, Jesús,Rivera, Joshua,Santana, Alberto,Briggs, Jon,Rheingold, Arnold L.,Matta, Jaime,Meléndez, Enrique

, p. 204 - 214 (2014)

Six ferrocenecarboxylates with phenyl, 4-(1H-pyrrol-1-yl)phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl as pendant groups were synthesized and fully characterized by spectroscopic, electrochemical and X-ray diffraction methods. The anti-proliferative activity of these complexes were investigated in hormone dependent MCF-7 breast cancer and MCF-10A normal breast cell lines, to determine the role of the para substituent on the phenoxy pendant group. The 4-fluorophenyl ferrocenecarboxylate is inactive in both cell lines while 4-(1H-pyrrol-1-yl)phenyl ferrocenecarboxylate is highly cytotoxic in both cell lines. 4-chlorophenyl and 4-bromophenyl ferrocenecarboxylates have moderate to good anti-proliferative activity in MCF-7 and low anti-proliferative activity on normal breast cell line, MCF-10A whereas the 4-iodophenyl analog is highly toxic on normal breast cell line. The phenyl ferrocenecarboxylate has proliferative effects on MCF-7 and is inactive in MCF-10A. Docking studies between the complexes and the alpha-estrogen receptor (ERα) were performed to search for key interactions which may explain the anti-proliferative activity of 4-bromophenyl ferrocenecarboxylate. Docking studies suggest the anti-proliferative activity of these ferrocenecarboxylates is attributed to the cytotoxic effects of the ferrocene group and not to anti-estrogenic effects.

N-Cobaltocenium Amide as Reactive Nucleophilic Reagent for Donor-Acceptor Bimetallocenes

Lauck, Maximilian,F?rster, Christoph,Heinze, Katja

, p. 4968 - 4978 (2017)

Deprotonation of the aminocobaltocenium ion [Cc-NH2]+ ([H-1]+) generates the nucleophilic imine CcNH (1). Reaction of 1 with acid chlorides R-COCl (R = Ph, Fc, and Cc+) yields the reference amide [Ph-CO-NH-Cc]+ (2+) and the amide-linked hetero- and homobimetallocenes [Fc-CO-NH-Cc]+ (3+) and [Cc-CO-NH-Cc]2+ (42+), respectively. Cation-anion interactions of charged amides 2+-42+ in the solid state and in solution are probed by single crystal X-ray diffraction and NMR and IR spectroscopy. Intramolecular metal-metal interactions in donor-acceptor heterobimetallocene 3+ and in mixed-valent homobimetallocene 4+ (prepared electrochemically) are discussed within the Marcus-Hush framework aided by spectroelectrochemical experiments and time-dependent density functional theory calculations.

Self-assembled bio-organometallic nanocatalysts for highly enantioselective direct aldol reactions

Yang, Xuejiao,Zhang, Liwei,Liang, Yaoyu,Wang, Yuefei,Shen, Yuhe,Xing, Qiguo,Qi, Wei,Wang, Pengfei,Liu, Xiao,Yang, Mengyao,Su, Rongxin,He, Mingxia,He, Zhimin

, p. 13735 - 13742 (2020)

Supramolecular nanocatalysts were designed for asymmetric reactions through the self-assembly process of a bio-organometallic molecule, ferrocene-L-prolinamide (Fc-CO-NH-P). Fc-CO-NH-P could self-assemble into versatile nanostructures in water, including nanospheres, nanosheets, nanoflowers, and pieces. In particular, the self-assembled nanoflowers exhibited a superior specific surface area, high stability, and delicate three-dimensional (3D) chiral catalytic active sites. The nanoflowers could serve as heterogeneous catalysts with an excellent catalytic performance toward direct aldol reactions in aqueous solution, achieving both high yield (>99%) and stereoselectivity (anti/syn = 97:3, ee% >99%). This study proposed a significant strategy to fabricate supramolecular chiral catalysts, serving as a favorable template for designing new asymmetric catalysts.

Synthesis and characterization of novel ferrocene-containing pyridylamine ligands and their ruthenium(II) complexes: Electronic communication through hydrogen-bonded amide linkage

Kojima, Takahiko,Noguchi, Daisuke,Nakayama, Tomoko,Inagaki, Yuji,Shiota, Yoshihito,Yoshizawa, Kazunari,Ohkubo, Kei,Fukuzumi, Shunichi

, p. 886 - 895 (2008)

Tris(2-pyridylmethyl)amine (TPA) derivatives with one or two ferrocenoylamide moieties at the 6-position of one or two pyridine rings of TPA were synthesized. The compounds, N-(6-ferrocenoylamide-2-pyridylmethyl)-N,N- bis(2-pyridylmethyl)amine (Fc-TPA; L1) and N,N-bis(6-ferrocenoylamide-2- pyridylmethyl)-N-(2-pyridylmethyl)amine (Fc2-TPA; L2), were characterized by spectroscopic methods, cyclic voltammetry, and X-ray crystallography. Their Ru(II) complexes were also prepared and characterized by spectroscopic methods, cyclic voltammetry, and X-ray crystallography. [RuCl(L1)(DMSO)]PF6 (1) that contains S-bound dimethyl sulfoxide (DMSO) as a ligand and an uncoordinated ferrocenoylamide moiety exhibited two redox waves at 0.23 and 0.77 V (vs ferrocene/ferrocenium ion as 0 V), due to Fc/Fc+ and Ru(II)/Ru(III) redox couples, respectively. [RuCl(L2)]PF6 (2) that contains both coordinated and uncoordinated amide moieties showed two redox waves that were observed at 0.27 V (two electrons) and 0.46 V (one electron), assignable to Ru(II)/Ru(III) redox couples overlapped with the uncoordinated Fc/Fc+ redox couple and the coordinated Fc/Fc+, respectively. In contrast to 2, an acetonitrile complex, [Ru(L2)(CH3CN)](PF6)2 (3), exhibited three redox couples at 0.26 and 0.37 V for two kinds of Fc/Fc+ couples, and 0.83 V for the Ru(II)/Ru(III) couple (vs ferrocene/ferrocenium ion as 0 V). In this complex, the redox potentials of the coordinated and the uncoordinated Fc-amide moieties were discriminated in the range of 0.11 V. Chemical two-electron oxidation of 1 gave [RuIIICl(L1 +)(DMSO)]3+ to generate a ferromagnetically coupled triplet state (S = 1) with J = 13.7 cm-1 (H = -JS1S 2) which was estimated by its variable-temperature electron spin resonance (ESR) spectra in CH3CN. The electron spins at the Ru(III) center and the Fe(III) center are ferromagnetically coupled via an amide linkage. In the case of 2, its two-electron oxidation gave the same ESR spectrum, which indicates formation of a similar triplet state. Such electronic communication may occur via the amide linkage forming the intramolecular hydrogen bonding.

Acylderivate der Ferrocenchalkogenole Fe(C5H5)(C5H4EH) und Fe(C5H4EH)2 (E=S, Se, Te)

Herberhold, Max,Leitner, Peter,Doernhoefer, Christine,Ott-Lastic, Jutta

, p. 281 - 290 (1989)

A series of nine ferrocene chalcogenol derivatives of the type Fe(C5H5)(C5H4EC(O)R) and of nine 1,1'-ferrocene dichalcogenol derivatives of the type Fe(C5H4EC(O)R)2 has been prepared in which the chalcogen (E=S, Se, Te) and the acyl group (C(O)R=benzoyl, 2-thenoyl, ferrocenoyl) were systematically varied.The crucial step of the synthesis includes insertion of the chalcogen E into the Li-C bond of the lithioferrocene to give the chalcogenolate intermediate Fe(C5H5)(C5H4ELi) or Fe(C5H4ELi)2, respectively, to be subsequently treated with the acyl chloride, RC(O)Cl.The 1H and 13C NMR spectra of the new compounds are discussed.

Cobalt-Catalyzed C?H Alkoxylation of Ferrocenes with Alcohols under Mild Conditions

Cheng, Jie,Yao, Qi-Jun,Yue, Qiang,Zhang, Zhuo-Zhuo,Zhou, Gang

, p. 3946 - 3951 (2021)

Herein we reported a protocol for synthesis of oxy-substituted ferrocenes via cobalt-catalyzed direct C?H alkoxylation under mild conditions. Notably, alcohol serves as an both alkoxide reagent and a solvent. Various ferrocene amides including estrone-derived ferrocene amide are compatible with these reaction conditions. Moreover, control experiments suggested that this alkoxylation might undergo a Co(III)/Co(IV)/Co(II) catalytic cycle. (Figure presented.).

Synthesis and catalytic performance of ferrocene-based compounds as burning rate catalysts

Zain-ul-Abdin,Wang, Li,Yu, Haojie,Saleem, Muhammad,Akram, Muhammad,Khalid, Hamad,Abbasi, Nasir M.,Khan, Rizwan Ullah

, (2017)

To overcome migration problems of ferrocene-based burning rate catalysts and to enhance burning rate of ammonium perchlorate (AP)-based propellants, eleven ferrocene-based compounds (1–11) were synthesized by the condensation reaction of ferrocenecarbonyl chloride with corresponding amines and alcohols. The synthesis of 1–11 was confirmed using 1H NMR, Fourier transform infrared and UV–visible spectroscopy. Their electrochemical properties were analyzed using cyclic voltammetry. The compounds showed redox behavior due to the presence of ferrocene. Their catalytic behavior in the thermal decomposition of AP was investigated using thermogravimetry (TG) and differential TG (DTG). In the presence of 5?wt% 1–11, the thermal decomposition temperature of AP was significantly decreased. TG and DTG analyses showed that 1–11 had a good catalytic effect in the thermal decomposition of AP. Anti-migration studies showed that migration of 1–11 was slower than that of 2,2-bis(ethylferrocenyl)propane (catocene) and ferrocene. The effect of the presence of polar elements like oxygen and nitrogen on anti-migration behavior of small ferrocene-based compounds was also investigated. Oxygen-containing compounds showed better anti-migration behavior than nitrogen-containing compounds.

Synthesis, Structural Reassignment, and Antibacterial Evaluation of 2,18-Seco-Lankacidinol B

Yao, Yanmin,Cai, Lingchao,Seiple, Ian B.

, p. 13551 - 13554 (2018)

Lankacidins are a group of polyketide natural products with activity against several strains of Gram-positive bacteria. We developed a route to stereochemically diverse variants of 2,18-seco-lankacidinol B and found that the stereochemical assignment at C4 requires revision. This has interesting implications for the biosynthesis of natural products of the lankacidin class, all of which possessed uniform stereochemistry prior to this finding. We have evaluated 2,18-seco-lankacidinol B and three stereochemical derivatives against a panel of pathogenic Gram-positive and Gram-negative bacteria.

A two-step palladium-catalyzed coupling scheme for the synthesis of ferrocene-labeled amino acids

Brosch, Oliver,Weyhermueller, Thomas,Metzler-Nolte, Nils

, p. 323 - 330 (2000)

This work describes a Pd-catalyzed coupling of ferrocene alkyne derivatives to iodo amino acids. Ferrocene carboxylic acid propargyl amides were easily obtained in high yield. The crystal structures of the propargyl amine derivative 3 and the 1,1-diethylpropargylamine derivative 4 have been determined by X-ray diffraction. Pd-catalyzed coupling to p-iodoanilide amino acids gave the corresponding ferrocene-labeled amino acid derivatives, which were easily purified by diethyl ether extraction in the case of the 1,1- diethyl derivatives 8. The coupling reaction did not require anhydrous solvents and tolerated a variety of functional groups present in peptides such as alcohols (8a, Ser), thioethers (8b, Met), disulfide bonds (cystine, 12) esters (as in the N-labeled Leu derivative 10) and of course amides. A minor by-product of the coupling reaction, namely the homo-dimer bis(ferrocene carboxylic acid propargylamide) 9, was identified in the crude reaction mixtures by mass spectrometry and independently synthesized by oxidative coupling (Glaser and Eglington) of 3. All new compounds were completely characterized spectroscopically, including 15N- and 2D NMR spectroscopy, Mossbauer spectroscopy and electrochemistry. This work introduces a versatile procedure for a selective functionalization of amino acids with organometallics at the C-terminus which is expected to be of general applicability to peptide chemistry.

Approach to ferrocenyl-podophyllotoxin analogs and their evaluation as anti-tumor agents

Beaupérin, Matthieu,Polat, Dilan,Roudesly, Fares,Top, Siden,Vessières, Anne,Oble, Julie,Jaouen, Gérard,Poli, Giovanni

, p. 83 - 90 (2017)

Podophyllotoxin is a natural product endowed of a high antimitotic activity and a high affinity for tubulin. Its action results in the cessation of cell division, inducing cell death. However, its high toxicity restrains its use as drug. To overcome this drawback, several chemical modifications of the native podophyllotoxin have been made. However, to date, no reports have so far been directed toward incorporation of a metallocene moiety. The search for new organometallic drugs is a central field in drug discovery, including the domain of cancer therapy. In particular, metallocenyl moieties are known to increase or decrease, depending on the degree of conjugation in the organometallic motif, the selectivity of drugs toward cancer cells. The conjugate organometallic compound reduces the damage of healthy tissues, yet permitting the selective desired antimitotic and cytotoxic effects of the active principle. We report here the synthesis of ferrocene-containing podophyllotoxin analogs and preliminary antiproliferative tests.

Electron Transfer between Amphiphilic Ferrocenes and Electrodes in Cationic Micellar Solution

Abbott, Andrew P.,Gounili, Giv,Bobbitt, James M.,Rusling, James F.,Kumosinski, Thomas F.

, p. 11091 - 11095 (1992)

Standard heterogeneous electron-transfer rate constants (k') for ferrocene (Fc) esters attached to the 2- and 5-carbon atoms (I and II) away from nitrogen on the hydrocarbon chain of dodecyltrimethylammonium ions were similar to each other and to ferrocene (Fc) in homogeneous organic solvent.However, in micellar solutions of cetyltrimethylammonium bromide (CTAB), differences were found for k' in the order Fc > I > II.Activation free energies from temperature dependences of k' and microenvironmental polarities from spectroscopic studies were similar for I and II in CTAB solutions, suggesting similar reorganization energies.The distance dependence of k' in micellar solution was consistent with predictions of Marcus theory using a through-space model with average distances of electron transfer estimated from molecular dynamics or a through-bond model assuming bonding of head groups to the electrode.Results suggest that CTAB adsorbed to the electrode helps to orient the electroactive surfactants with alkylammonium head groups down on the Pt surface prior to electron transfer.Electron transfer to Pt from Fc in cationic micellar solutions occurs over a shorter distance than for I.

Tris(2-aminoethyl)amine-based ferrocene-terminated dendrimers as burning rate catalysts for ammonium perchlorate-based propellant decomposition

Zain-ul-Abdin,Wang, Li,Yu, Haojie,Khan, Rizwan Ullah,Ullah, Raja Summe,Haroon, Muhammad

, (2018)

Ferrocene-based derivatives show potential application as burning rate catalysts (BRCs) for solid composite propellants. However, migration problems of simple ferrocene-based derivatives limit their application as BRCs in solid composite propellants. To o

Electrochemistry at the air/water interface. Lateral diffusion of an octadecylferrocene amphiphile in langmuir monolayers

Charych, Deborah H.,Landau, Ehud M.,Majda, Marcin

, p. 3340 - 3346 (1991)

A new electrochemical method is described to investigate the dynamics of lateral diffusion processes in Langmuir monolayers at the air/water interface. The key element of this technique is a gold microband electrode, which can be positioned in the plane of the water surface and which functions as a 1D electrode in contact with a 2D collection of electroactive, water insoluble molecules. Investigations of N-octadecylferrocenecarboxamide (C18Fc) monolayers and mixed monolayers of C18Fc and octadecanol on 0.05 M HClO4 at 28 °C showed that they remain fluid without undergoing any phase transitions, in a surface concentration range of 3.3 × 10-10 to 7 × 10-11 mol/cm2. Lateral diffusion of C18Fc can be modeled as a 2D fluid of hard disks with the cross sectional area equal to the projected area of the ferrocene head group. The diffusion coefficient increases linearly with the average free area per molecule on the water surface.

Preparation and biodistribution of 1-((2-methoxyphenyl) piperazine)ferrocenecarboxamide labeled with technetium-99m as a potential brain receptor imaging agent

Saied, Nadia Malek,Mejri, Najoua,El Aissi, Radhia,Benoist, Eric,Saidi, Mouldi

, p. 280 - 288 (2015)

The goal of this study is to develop a novel brain receptor imaging agent. This study reports the synthesis, characterization and the biological evaluation of 1-((2-methoxyphenyl) piperazine)ferrocenecarboxamide labeled with technetium-99 m (99mTc-MP). The 99mTc-MP was obtained quickly (radiolabelling time 99mTc-complex, characterized by HPLC (20-50% ACN of 0 at 5 min then 50% ACN of 5 at 17 min to finally with 50 at 20% ACN of 17 at 20 min), is stable, neutral and lipophilic enough to cross the blood-brain barrier which was confirmed by octanol/water partition coefficient (LogP = 1.82). In vivo biodistribution indicated that this complex had exceptional brain uptake (2.47% ID/g at 5 min and 0.75% ID/g at 60 min). The distribution of the activity at 15 min post-injection in various rat brain regions showed a higher accumulation in the hippocampus area. After blocking with 8-hydroxy-2-(dipropylamino) tetralin, the uptake of hippocampus was decreased significantly from 0.87% ID/g to 0.21% ID/g at 15 min p.i., while the cerebellum had no significant decrease. The new 99mTc-cyclopentadienyltricarbonyl technetium complex reported here showed promising biological results, making it an interesting starting point for the development of a new 99mTc-complex as brain receptor imaging agent.

Chiral oxazolinylferrocene-phosphine hybrid ligand for the asymmetric hydrosilylation of ketones

Nishibayashi, Yoshiaki,Segawa, Kyohei,Ohe, Kouichi,Uemura, Sakae

, p. 5486 - 5487 (1995)

A new type of chiral oxazolinylferrocene - phosphine hybrid is a very effective ligand for Rh(I)-catalyzed asymmetric hydrosilylation of simple ketones to give the corresponding sec-alcohols (91% ee) after acid hydrolysis. Similar reactions also proceed highly selectively (96% ee) by use of Ir(I) catalyst, but the configuration of the products is completely reverse.

Assessment of the nematocidal activity of metallocenyl analogues of monepantel

Hess, Jeannine,Patra, Malay,Jabbar, Abdul,Pierroz, Vanessa,Konatschnig, Sandro,Spingler, Bernhard,Ferrari, Stefano,Gasser, Robin B.,Gasser, Gilles

, p. 17662 - 17671 (2016)

In this study, we present the design, synthesis, characterization and biological evaluation of structurally new ferrocenyl and ruthenocenyl derivatives of the organic anthelmintic monepantel (Zolvix). All seven metallocenyl derivatives prepared (4a/b, 5a/b, 6a/b and 7) were isolated as racemates and characterized by 1H, 13C and 19F NMR spectroscopies, mass spectrometry, IR spectroscopy and elemental microanalysis. The molecular structures of four compounds (4a/b, 6a and 7) were further confirmed by X-ray crystallography. The biological activities of the organometallic intermediates (4a/b) and organometallic derivatives of monepantel (5a/b, 6a/b and 7) were evaluated in vitro using parasitic nematodes of major importance in livestock, namely Haemonchus contortus and Trichostrongylus colubriformis. Two ferrocenyl compounds (4a and 6a) showed nematocidal activity, while the analogous ruthenocenyl compounds (4b and 6b) were not active at the highest concentration tested (10 μg mL-1). In order to obtain insight into the difference in activity between ferrocenyl and ruthenocenyl derivatives, the potential of the compounds for reactive oxidative species (ROS) production in live cells was assessed. Interestingly, neither the ferrocenyl nor the ruthenocenyl compounds (4a/b and 6a/b) produced significant ROS in HeLa cells when checked after 22 h, potentially indicating a redox-independent activity of 4a and 6a on the parasites. The selectivity of the compounds on parasites was confirmed by investigating their cytotoxicity profiles. None of these compounds was toxic either to HeLa or MRC-5 cells. Thus, 4a and 6a could be considered as interesting leads for further development of new classes of anti-parasitic agents.

Palladacycles Based on 8-Aminoquinoline Carboxamides of Cobalt and Iron Sandwich Compounds and a New Method to α-Alkylate Cp Rings of Metal Sandwich Carboxamides

Singh, Jatinder,Deb, Mayukh,Elias, Anil J.

, p. 4946 - 4951 (2015)

Reactions of {η5-C5H4[C(O)Cl]}Co(η4-C4Ph4) and {η5-C5H4[C(O)Cl]}Fe(η5-Cp) with 8-aminoquinoline resulted in cobalt and iron sandwich derived carboxamides. The reaction of these carboxamides with Pd(OAc)2 in acetonitrile resulted in αC-H activation of the Cp rings of the sandwich compounds and formation of novel palladacycles 3 and 4, having both N-H and one α-C-H hydrogen atom of the Cp ring displaced and palladium forming a square planar complex with acetonitrile as the fourth ligand. These air-stable palladacycles reacted with MeI and EtI in acetic acid, resulting in mono- and 2,5-di-α-alkylated sandwich carboxamides, thereby providing a new method to realize Cp-multisubstituted sandwich compounds. Selectivity in α-substitution was observed in the presence of NaHCO3. The cobalt sandwich carboxamide 1, the new palladacycles 3 and 4, and the 2,5-dimethylated cobalt sandwich carboxamide 5 have also been structurally characterized using single-crystal X-ray structural studies.

Synthesis and properties of stimuli-responsive ferrocene-and azobenzene-based copolymers P(FHEMA-co-MAAT)s

Khan, Amin,Wang, Li,Yu, Haojie,Haroon, Muhammad,Ullah, Raja Summe,Nazir, Ahsan,Elshaarani, Tarig,Usman, Muhammad,Fahad, Shah,Naveed, Kaleem-ur-Rehman

, p. 124 - 133 (2019)

Three novel polymers (P(FHEMA-co-MAAT)s) having redox and photoresponsive moieties were prepared by free radical polymerization. The structures and molecular weights of the synthesized copolymers were characterized by nuclear magnetic resonance (1H NMR) and gel permeation chromatography (GPC) respectively. Thermal properties, optical features and electroactive properties were studied with the help of thermogravimetric (TG), differential thermogravimetric (DTG) analysis, ultraviolet-visible spectroscopy (UV-vis) and cyclic voltammetry (CV). It was seen that synthesized copolymers had excellent redox and photoresponsive properties. These results exhibited that these polymers can be applied further for redox/photo responsive information storage devices.

Amide-Directed Cobalt(III)-Catalyzed C-H Amidation of Ferrocenes

Huang, Dan-Ying,Yao, Qi-Jun,Zhang, Shuo,Xu, Xue-Tao,Zhang, Kun,Shi, Bing-Feng

, p. 951 - 954 (2019)

The amide-directed cobalt(III)-catalyzed C-H amidation of ferrocene carboxamides using 1,4,2-dioxazol-5-ones as robust and efficient amidating reagents has been developed. This reaction proceeds efficiently under mild reaction conditions with good functional group tolerance, providing expedient access to a broad range of ferrocenes containing a nitrogen group on the Cp ring.

Synthesis of ferrocene[c]pyridin-2(1H)-one derivatives via Pd(II)-catalyzed C–H activation reaction under air

Liu, Hua-Yu,Mou, Rui-Qi,Sun, Chuan-Zhi,Zhang, Sheng-Yan,Guo, Dian-Shun

, p. 4676 - 4679 (2016)

A Pd(II)-catalyzed C–H activation annulation under air has been successfully developed for efficient synthesis of ferrocene[c]pyridin-2(1H)-one derivatives with high yields and good regiochemistry. This method shows highly atom- and step-economical access to prepare ferrocene-fused heterocycles under mild conditions.

Directed Iron-Catalyzed ortho-Alkylation and Arylation: Toward the Stereoselective Catalytic Synthesis of 1,2-Disubstituted Planar-Chiral Ferrocene Derivatives

Schmiel, David,Butensch?n, Holger

, p. 4979 - 4989 (2017)

The iron-catalyzed directed ortho-functionalization of arenes developed to an important method in the field of C-H activation. On the other hand, the iron-catalyzed ortho-functionalization of ferrocenes bearing ortho-directing groups (ODGs) has scarcely been investigated. Herein we present the iron-catalyzed ortho-alkylation and -arylation of ODG-substituted ferrocenes bearing a bidentate ODG with the formation of racemic 1,2-disubstituted ferrocenes in up to 94% yield. The approach toward an enantioselective iron-catalyzed C-H activation resulted in an ortho-phenylation with a promising enantiomeric excess of 46%. The first iron-catalyzed diastereoselective ortho-methylation gave an excellent diastereomeric excess of ≥99%.

Direct Synthesis of Enamides via Electrophilic Activation of Amides

Berger, Martin,Kaiser, Daniel,Maulide, Nuno,Spie?, Philipp

supporting information, p. 10524 - 10529 (2021/07/28)

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.

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