Ferrocenecarboxylic acid and microwave-assisted synthesis of ferrocenoyl hydrazones

Kulikov, V. N.; Nikulin, R. S.; Arkhipov, Dmitry E.; Rodionov, А. N.; Бабусенко, Е. С.; Kovalenko, L. V.; Belousov, Yu. A.

doi:10.1007/s11172-017-1768-x

Cited by 7 publications

(7 citation statements)

References 10 publications

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“…Ferrocenecarboxylic acid (FcCO 2 H), [14] ferrocenylvinyl ketone (Fc‐Vin), [15] tetraphenylporphyrin (H 2 TPP), as well as ferrocene‐porphyrins, in which ferrocene is bounded to porphyrin via a heterocyclic fragment, pyrazole (FcPzNHH 2 TPP and Fc( i Pr)PzNHH 2 TPP) or triazole (FcTzNHH 2 TPP) (Figure 1). In vitro tests with A. ferrooxidans using different ultrasound irradiation revealed unexpected results (Table 1).…”

Section: Resultsmentioning

confidence: 99%

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Ferrocenes and Porphyrins as Acidithiobacillus ferrooxidans Growth Activators under Ultrasound Irradiation

Rogatkina,

Mazina,

Rodionov

et al. 2023

ChemistrySelect

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Acidithiobacillus ferrooxidans are beneficial bacteria for bioleaching in the mining industry to extract useful fractions from tons of waste. These bacteria are able to oxidize ferrous iron (Fe2+) to ferric iron (Fe3+) and use the released energy to assimilate carbon from carbon dioxide or carbonates, and can be used in the desulfurization of coal and gas. In this regard, activators of the growth of these bacteria may be useful. During the experiments on these bacterial strains, an unexpected effect of growth activation was revealed. This gives rise to further research in this direction and the identification of patterns of “structure‐activity” derivatives of ferrocene and porphyrins in relation to A. ferrooxidans.

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Section: Resultsmentioning

confidence: 99%

“…216 °C (215-217 °C). [14] Acryloylferrocene (Fc-Vin) was prepared according to modifications of previously reported. [15] 3-chloropropanoylferrocene (1.0 mmol) and DIPEA (1.0 mmol) was diluted in toluene (5 mL).…”

Section: Ferrocenecarboxylic Acid (Fcco 2 Hmentioning

confidence: 99%

Ferrocenes and Porphyrins as Acidithiobacillus ferrooxidans Growth Activators under Ultrasound Irradiation

Rogatkina,

Mazina,

Rodionov

et al. 2023

ChemistrySelect

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“…First, sodium ferrocenylcarboxylate, 2 , a well‐known compound, [33] was synthesized in a biphasic CH 2 Cl 2 /water system upon reaction of a CH 2 Cl 2 solution of ferrocenylcarboxylic acid 1 with an aqueous NaOH solution under ambient conditions overnight (Equation .…”

Section: Resultsmentioning

confidence: 99%

“…Both monodentate and bidentate coordination of acetate and other carboxylates were disclosed and found to depend on the ligand concentration at the AuNP surface. [10] The synthesis, [32,33] electrochemistry, [21,34] [a] Dr. C. Wang, + A. Brudo, + L. Ducrot, + Dr. F. Fu, Dr. J. Ruiz, Prof. Dr and use as ligands in clusters [35] and polynuclear chemistry [36,37] of ferrocene mono-and dicarboxylate have already been reported, unlike their association in NPs.…”

Section: Introductionmentioning

confidence: 99%

Generation of Catalytically Active Gold Nanocrystals in Water Induced with Ferrocene Carboxylate

et al. 2021

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The fabrication and properties of anisotropic gold nanoparticles (AuNPs) are of great interest from fundamental and application standpoints. Whereas various neutral ferrocene derivatives have been shown to reduce Au III to Au 0 NPs owing to slightly exergonic electron transfer in biphasic systems, the question remained open for water soluble ferrocenes containing electron withdrawing substituents increasing the Fe III /Fe II oxidation potential. Here, it is shown that reaction of sodium ferrocene carboxylate, NaFcCO 2 , alone, does not reduce H[Au III Cl 4 ] to stable AuNPs under ambient conditions in water. On the other hand, reaction between NaFcCO 2 and H[Au III Cl 4 ] in water in the presence of poly (vinyl pyrrolidone) (PVP), citrate or other 1,2,3triazole (trz)-containing stabilizers is shown to produce catalytically active Au nanocrystals with various shapes. EDX results confirm the fixation of the ferrocenyl carboxylate ligand onto the AuNP surface. 4-nitrophenol reduction to 4-aminophenol by Na [BH 4 ] in water proceeds in the presence of the various stabilizers, without induction time in most cases, which confirms the weakness of the ferrocenyl carboxylate ligand bonded to the AuNP surface and the favorable role of ferrocenyl carboxylate ligand for catalysis at the AuNP surface.

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“…In 2017, Kulikov et al described a microwave-assisted synthesis of ferrocenoyl hydrazones 241 starting from ferrocene carbohydrazide 240 and aldehydes in EtOH (Scheme 63). 170 After a few seconds of heating, compounds 241 were recovered in very high yields (93−100% yield) after a simple filtration of the resulting precipitate. Conventional heating led to higher reaction times and lower yields, presumably due to partial decomposition of either 240 or 241 under prolonged heating.…”

Section: Microwave Proceduresmentioning

confidence: 99%

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

et al. 2019

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Organometallic complexes: these two words jump to the mind of the chemist and are directly associated with their utility in catalysis or as a pharmaceutical. Nevertheless, to be able to use them, it is necessary to synthesize them, and it is not always a small matter. Typically, synthesis is via solution chemistry, using a roundbottom flask and a magnetic or mechanical stirrer. This review takes stock of alternative technologies currently available in laboratories that facilitate the synthesis of such complexes. We highlight five such technologies: mechanochemistry, also known as solvent-free chemistry, uses a mortar and pestle or a ball mill; microwave activation can drastically reduce reaction times; ultrasonic activation promotes chemical reactions because of cavitation phenomena; photochemistry, which uses light radiation to initiate reactions; and continuous flow chemistry, which is increasingly used to simplify scaleup. While facilitating the synthesis of organometallic compounds, these enabling technologies also allow access to compounds that cannot be obtained in any other way. This shows how the paradigm is changing and evolving toward new technologies, without necessarily abandoning the round-bottom flask. A bright future is ahead of the organometallic chemist, thanks to these novel technologies. CONTENTS1. Introduction 7530 2. Technologies 7530 2.1. Grinding and Milling 7530 2.2. Microwave Irradiation 7531 2.3. Ultrasound Activation 7531 2.4. Photochemistry 7532 2.5. Continuous Flow 7532 3. Contribution of Each Technology Compared to Classical Syntheses 7533 4. Lithium and Magnesium 7534 4.1. Mechanochemical Access to Grignard Reagents 7534 4.2. Microwave Irradiation for the Synthesis of Magnesium Complexes 7534 4.3. Ultrasonic Procedures 7535 4.4. Continuous Flow Syntheses 7535 5. Groups 2, 3, 4, and 5 7537 5.1. Mechanochemical Procedures for Complexes of Groups 2, 3, and 4 7537 5.2. Microwave Irradiation for the Synthesis of Vanadium Complexes 7537 5.3. Synthesis of Vanadium Complexes Using Ultrasound 7538 6. Group 6 7538 6.1. Mechanosynthesis of Molybdenum and Chromium Complexes 7538 6.2. Microwave Irradiation for the Synthesis of Group 6 Metal Complexes 7539 6.3. Photochemistry for Synthesis of Group 6 Metal Complexes 7543 6.4. Continuous Flow Chemistry for Synthesis of Chromium Complexes 7545 7. Group 7 7545 7.1. Mechanosynthesis of Rhenium Complexes 7545 7.2. Microwave Irradiation for the Synthesis of Group 7 Metal Complexes 7546 7.3. Photochemical Synthesis of Manganese and Rhenium Complexes 7549 8. Group 8 7550 8.1. Synthesis of Iron and Ruthenium Complexes Using Ball Milling 7550 8.2. Microwave Procedures 7552 8.3. Ultrasonic Irradiation for Iron Complexes 7562 8.4. Syntheses of Iron and Ruthenium Complexes Using Photochemistry 7563 8.5. Continuous Flow Conditions to Prepare Iron and Ruthenium Complexes 7566 9. Group 9 7566 9.1. Synthesis of Cobalt and Rhodium Complexes by Mechanochemistry 7566 9.2. Procedures Using Microwave Irradiation 7569 9.3. Photochemical Synthesis of Iridium Complexes 7...

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Ferrocenecarboxylic acid and microwave-assisted synthesis of ferrocenoyl hydrazones

Cited by 7 publications

References 10 publications

Ferrocenes and Porphyrins as Acidithiobacillus ferrooxidans Growth Activators under Ultrasound Irradiation

Ferrocenes and Porphyrins as Acidithiobacillus ferrooxidans Growth Activators under Ultrasound Irradiation

Generation of Catalytically Active Gold Nanocrystals in Water Induced with Ferrocene Carboxylate

Alternative Technologies That Facilitate Access to Discrete Metal Complexes

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