Electrochemical Fluorination

Ignat’ev, Nikolai

doi:10.1016/b978-0-12-803740-9.00004-4

Cited by 14 publications

(19 citation statements)

References 163 publications

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“…This procedure can only be performed with specialized equipment for electrosynthesis and with extreme caution as short chain trialkylphosphines are pyrophoric and HF is quite corrosive. Another electrochemical fluorination method from tris(perfluoroalkyl)phosphine oxides starting material is also quite dangerous as it involves the generation of a highly toxic gas byproduct, oxygen difluoride . In addition, the absence of commercially available HFAP is also an issue hindering FAP ionic liquid production.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Properties of Methoxy and Nitrile Functionalized Imidazolium Tris(pentafluoroethyl)trifluorophosphate Ionic Liquids

et al. 2018

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An alternative and more benign method was employed to synthesize tris(pentafluoroethyl)trifluorophosphate (FAP) ionic liquids (ILs). Ion exchange chromatography was used instead of the typical electrochemical fluorination developed by Ignat'ev and co-workers. The resulting procedure is simple and can be readily performed, as the use of corrosive hydrofluoric acid and the production of toxic and explosive byproducts were circumvented. Functionalization of the alkyl group of the imidazolium cation with a methoxy and a nitrile moiety was employed to observe changes in properties. The success of the synthesis was confirmed by 1 H, 19 F, and 31 P NMR, IR, and UV−vis spectroscopy techniques. Quantitative product yields of approximately 80% (w/w) were obtained. The water content and viscosity values of the synthesized FAP-based ILs were found to be lower compared to other fluorinecontaining ionic liquids. Thermal analyses resulted in high thermal degradation temperatures greater than 573.15 K. Electrochemical analyses showed potential windows of values greater than 5.0 V, indicating electrochemical stability. On the basis of the basic properties observed, the FAP-based ILs synthesized in this study may be useful as gas absorbents, electrolytes, and other applications, especially those involving extended temperature ranges.

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Section: Introductionmentioning

confidence: 99%

Syntheses and Properties of Methoxy and Nitrile Functionalized Imidazolium Tris(pentafluoroethyl)trifluorophosphate Ionic Liquids

et al. 2018

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“…The Simons process is an electrochemical method with an exceptionally high functional group tolerance for the generation of industrially important compounds such as triflic acid or perfluorobutane sulfonic acid (PFBS) from their non-fluorinated derivatives. 1–6 PFBS, the follow-up and potentially less toxic homologue 6,7 of perfluorooctane sulfonic acid (PFOS; annual production of up to 4500 t), 8 was similarly used to protect fabrics from water, soil and stain. 1,3,6 A row of functionalized perfluorocarbons including perfluorooctyl bromide (PFOB) are of medical interest as oxygen carriers or “blood substitutes”.…”

mentioning

confidence: 99%

“…1–6 PFBS, the follow-up and potentially less toxic homologue 6,7 of perfluorooctane sulfonic acid (PFOS; annual production of up to 4500 t), 8 was similarly used to protect fabrics from water, soil and stain. 1,3,6 A row of functionalized perfluorocarbons including perfluorooctyl bromide (PFOB) are of medical interest as oxygen carriers or “blood substitutes”. 1,9 Within the broad range of applications for triflic acid, 10,11 it depicts the starting material for the production of lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), which is commonly used in electrolytes of Li-ion batteries.…”

mentioning

confidence: 99%

“…1,3,6 A row of functionalized perfluorocarbons including perfluorooctyl bromide (PFOB) are of medical interest as oxygen carriers or “blood substitutes”. 1,9 Within the broad range of applications for triflic acid, 10,11 it depicts the starting material for the production of lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), which is commonly used in electrolytes of Li-ion batteries. 11,12 Given the value of the fluorinated compounds produced, 1,3,5,6,13 the Simons process is performed with abundant resources, using anhydrous hydrogen fluoride (aHF) as fluoride source, electricity, nickel electrodes, and simple organic starting materials.…”

mentioning

confidence: 99%

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Unravelling highly oxidized nickel centers in the anodic black film formed during the Simons process by in situ X-ray absorption near edge structure spectroscopy

Senges,

Buzanich,

Lindič

et al. 2024

Chem. Sci.

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“…[55][56][57] Selective electrochemical fluorination in the synthesis of heterocycles, 58 solvent effects in ECF, 59 and the use of ionic liquids by Fuchigami. 60,61 Recent reviews include Ignat'ev, [62][63][64] synthesis of a fluorinated conjugated polymer by Inagi, 65 and recent advances in ionic liquid by Fuchigami. 66 This review presents, a broad picture of recent development and strategic evolution of electrochemical fluorination from the past decade by highlighting the future perspectives to face the encounters associated with this field.…”

mentioning

confidence: 99%

Review—Electrochemical Strategies for Selective Fluorination of Organic Compounds

Thadathil

Varghese

Radhakrishnan

2021

J. Electrochem. Soc.

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The conventional methods for carrying out fluorination of organic compounds are typically conducted using a pre-modified starting material, usually expensive and toxic reagents. In this regard, electrochemical fluorination has been recognized as a sustainable and scalable strategy. Electrofluorination has proven to be an environmentally benign, highly effective, and versatile platform for the synthesis of selective organofluorine compounds under mild conditions. This review provides an overview on the use of anodic electrochemical methods for vicinal difluorination, iodofluorination, fluoroalkynylation, fluorodecarboxylation, fluoro desulfurization, radiofluorination, and synthesis of fluorinated heterocycles. Modern advances in the field of electrochemical fluorination, such as ionic liquids mediated electrochemical fluorination, triethylammonium halides, mixed non-aqueous solvents, alkali–metal fluoride, and split-bipolar electrodes in the field of electrochemical fluorination are also discussed.

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Electrochemical Fluorination

Cited by 14 publications

References 163 publications

Syntheses and Properties of Methoxy and Nitrile Functionalized Imidazolium Tris(pentafluoroethyl)trifluorophosphate Ionic Liquids

Syntheses and Properties of Methoxy and Nitrile Functionalized Imidazolium Tris(pentafluoroethyl)trifluorophosphate Ionic Liquids

Unravelling highly oxidized nickel centers in the anodic black film formed during the Simons process by in situ X-ray absorption near edge structure spectroscopy

Review—Electrochemical Strategies for Selective Fluorination of Organic Compounds

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