Electrochemical radiofluorination. Part 2. Anodic monofluorination of substituted benzenes using [18F]fluoride

Reischl, Gerald; Kienzle, Gabriele; Machulla, H.-J.

doi:10.1016/s0969-8043(03)00093-9

Cited by 16 publications

(7 citation statements)

References 12 publications

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“…Recently we and others have reported on the electrochemical 18 F-fluorination of aromatic compounds (Reischl et al, 2002; Reischl et al, 2003; Kienzle et al, 2005). 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.…”

Section: Introductionmentioning

confidence: 96%

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: 96%

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

Waldmann

Lebedev

Allison

et al. 2017

Applied Radiation and Isotopes

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“…Among the methods to generate an electron-poor carbon in arenes (Ermert et al, 2004; Gao et al, 2012; Nozaki and Tanaka, 1967; Shiue et al, 1984), electrochemical anodic oxidation is technically elegant because the reactions can be carried out under mild conditions and there is no hazardous chemical oxidant required (Fuchigami and Inagi, 2011). Radiofluorination of complex molecules by electrochemistry has been done under galvanostatic conditions by Reischl et al in their series publications (Kienzle et al, 2005; Reischl et al, 2002, 2003). Different from the umpolung strategy (Gao et al, 2012), the oxidation effect can be precisely controlled by the applied potential on the working electrode.…”

Section: Introductionmentioning

confidence: 99%

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

Wang

Alfeazi

et al. 2014

Applied Radiation and Isotopes

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An electrochemical method with the ability to conduct 18F-fluorination of aromatic molecules through direct nucleophilic fluorination of cationic intermediates is presented in this paper. The reaction was performed on a remote-controlled automatic platform. Nucleophilic electrochemical fluorination of tert-butyloxycarbonyl (Boc) protected catechol, an intermediate model molecule for the positron emission tomography (PET) probe (3,4-dihydroxy-6-[18F]fluoro-l-phenylalanine), was performed. Fluorination was achieved under potentiostatic anodic oxidation in acetonitrile containing Et3N · 3HF and other supporting electrolytes. Radiofluorination efficiency was influenced by a number of variables, including the concentration of the precursor, concentration of Et3N · 3HF, type of supporting electrolyte, temperature and time, as well as applied potentials. Radiofluorination efficiency of 10.4 ± 0.6% (n = 4) and specific activity of up to 43 GBq/mmol was obtained after 1 h electrolysis of 0.1 M of 4-tert-butyl-diboc-catechol in the acetonitrile solution of Et3N · 3HF (0.033 M) and NBu4PF6 (0.05 M). Density functional theory (DFT) was employed to explain the tert-butyl functional group facilitation of electrochemical oxidation and subsequent fluorination.

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“…In a following paper, Reischl et al. extended the method to other benzene derivatives such as fluorobenzene, chlorobenzene, bromobenzene, tert ‐butylbenzene, and acetophenone [30] . Two possible reaction products were found by the authors, the H‐substitution or the substituent replacement (Table 1).…”

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 radiofluorination. Part 2. Anodic monofluorination of substituted benzenes using [18F]fluoride

Cited by 16 publications

References 12 publications

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

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

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

Electrochemical Radiofluorination of Small Molecules: New Advances

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