Electrochemical nucleophilic synthesis of di-tert-butyl-(4-[18F]fluoro-1,2-phenylene)-dicarbonate

He, Qinggang; Wang, Ying; Alfeazi, Ines; Sadeghi, Saman

doi:10.1016/j.apradiso.2014.06.013

Cited by 20 publications

(18 citation statements)

References 22 publications

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“…The concept was exemplified by the synthesis of di- tert -butyl-(4-[ 18 F]fluoro-1,2-phenylene)-dicarbonate ( 1 ) – a model compound for synthesis of [ 18 F]F-DOPA (Fig. 1) (He et al, 2014). …”

Section: Introductionmentioning

confidence: 99%

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

Waldmann

Lebedev

Allison

et al. 2017

Applied Radiation and Isotopes

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Electrochemical 18F-fluorination of organic compounds provides a means to synthesize Positron-Emission-Tomography (PET) tracers difficult to obtain otherwise. Here, the first automated synthesizer that enables radiolabeling through carrier-added electrochemical 18F-fluorination is described. The system provides capabilities for all necessary operations such as drying of cyclotron derived [18F]fluoride, electrochemical incorporation of the radioisotope into a precursor molecule, subsequent reactions such as protecting group removals, HPLC-purification and formulation of the final tracer. Demonstrated is the aliphatic electrochemical 18F-fluorination of methyl 2-(phenylthio)acetate.

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Section: Introductionmentioning

confidence: 99%

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

Waldmann

Lebedev

Allison

et al. 2017

Applied Radiation and Isotopes

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“…Electrochemical oxidation can create an electron‐poor carbon, potentially without the need for chemical modification, preparing the organic molecules for nucleophilic fluorination ,. Fluorine atoms can be added to organic compounds in one step under mild conditions using electrochemistry, even for electron rich moieties such as aromatic and heteroaromatic rings, without the need to have leaving groups ,…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Flash Fluorination and Radiofluorination

et al. 2018

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A new method for rapid late-stage fluorination using the cation pool technique is presented. Fluorination and no-carrier-added radiofluorination of methyl (phenylthio) acetate, methyl 2-(methylthio) acetate, and methyl 2-(ethylthio) acetate were performed. The carbocations formed through electrochemical oxidation were stabilized by using a divided electrochemical cell and 2,2,2-trifluoroethanol (TFE) as the solvent at −20 °C. At the end of electrolysis, either stable-isotope [19F]fluoride or no-carrier-added radioactive [18F]fluoride was added to the reaction mixture to form the fluorinated or radiofluorinated product.

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“…Motivated by the seminal work of Reischl and coworkers, we performed the electrochemical radiosynthesis of di‐ tert ‐butyl‐(4‐[ 18 F]fluoro‐1,2‐phenylene)‐dicarbonate, which is a model compound for the widely used clinical PET tracer [ 18 F]F‐DOPA [32] . The influence of the tert ‐butyl leaving group on the radiofluorination process was evaluated and explained with the help of density functional theory (DFT) (Scheme 4).…”

Section: Electrochemical (Radio)fluorinationmentioning

confidence: 99%

Electrochemical Radiofluorination of Small Molecules: New Advances

Hernández-Valdés

Sadeghi

2021

The Chemical Record

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The development of new 18F‐based radiopharmaceuticals constantly demands innovations in the search for new radiofluorination methods. [18F]fluoride is the simplest and most convenient chemical form of the isotope for the synthesis of 18F‐based radiopharmaceuticals. The ease of production and handling, as well as the possibility of obtaining high molar activities, makes it the preferred choice for radiofluorination. However, the use of [18F]fluoride in late‐stage radiofluorination comes with challenges, especially for the radiolabeling of electron‐rich molecules where SN2 and SNAr reactions are not suitable. New developments in fluorination chemistry have been extensively studied to overcome these difficulties. Selective electrochemical oxidation of precursors, using a controlled potential, is one method to create reactive intermediates and overcome the activation energy required for nucleophilic fluorination of electron‐rich moieties. This method has been used for years in cold fluorination of organic molecules and more recently has been adapted as an alternative to traditional radiofluorination methods. Although relatively young, this field stands out as a promising route for the synthesis of new PET probes as well as fluorinated pharmaceuticals. This review focuses on recent advances in electrochemical radiofluorination as an alternative for the late‐stage radiolabeling of organic molecules.

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Electrochemical nucleophilic synthesis of di-tert-butyl-(4-[18F]fluoro-1,2-phenylene)-dicarbonate

Cited by 20 publications

References 22 publications

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

An automated synthesizer for electrochemical 18F-fluorination of organic compounds

Electrochemical Flash Fluorination and Radiofluorination

Electrochemical Radiofluorination of Small Molecules: New Advances

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