Ring opening of epoxides with [<sup>18</sup>F]FeF species to produce [<sup>18</sup>F]fluorohydrin PET imaging agents

Verhoog, Stefan; Brooks, Allen F.; Winton, Wade; Viglianti, Benjamin L.; Sanford, Melanie S.; Scott, Peter J. H.

doi:10.1039/c9cc02779c

Cited by 14 publications

(7 citation statements)

References 46 publications

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“…In 2014, building on the pioneering work of Bruns and Haufe (2014). Doyle reported the opening of racemic epoxides with (R,R)-[ 18 F](salen)Co(III)F under mild conditions to access radiotracers containing a [ 18 F]fluorohydrin moiety (Verhoog et al 2019). Advantageously, (R,R)-[ 18 F] (salen)Co(III)F was prepared by direct elution of [ 18 F]F − from the QMA cartridge using air-stable (R,R)-(salen)CoOTs.…”

Section: Csp 3 -F Bond Formationmentioning

confidence: 99%

Closing the gap between 19F and 18F chemistry

Ajenjo

Destro

Cornelissen

et al. 2021

EJNMMI radiopharm. chem.

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Positron emission tomography (PET) has become an invaluable tool for drug discovery and diagnosis. The positron-emitting radionuclide fluorine-18 is frequently used in PET radiopharmaceuticals due to its advantageous characteristics; hence, methods streamlining access to 18F-labelled radiotracers can make a direct impact in medicine. For many years, access to 18F-labelled radiotracers was limited by the paucity of methodologies available, and the poor diversity of precursors amenable to 18F-incorporation. During the last two decades, 18F-radiochemistry has progressed at a fast pace with the appearance of numerous methodologies for late-stage 18F-incorporation onto complex molecules from a range of readily available precursors including those that do not require pre-functionalisation. Key to these advances is the inclusion of new activation modes to facilitate 18F-incorporation. Specifically, new advances in late-stage 19F-fluorination under transition metal catalysis, photoredox catalysis, and organocatalysis combined with the availability of novel 18F-labelled fluorination reagents have enabled the invention of novel processes for 18F-incorporation onto complex (bio)molecules. This review describes these major breakthroughs with a focus on methodologies for C–18F bond formation. This reinvigorated interest in 18F-radiochemistry that we have witnessed in recent years has made a direct impact on 19F-chemistry with many laboratories refocusing their efforts on the development of methods using nucleophilic fluoride instead of fluorination reagents derived from molecular fluorine gas.

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Section: Csp 3 -F Bond Formationmentioning

confidence: 99%

Closing the gap between 19F and 18F chemistry

Ajenjo

Destro

Cornelissen

et al. 2021

EJNMMI radiopharm. chem.

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“…These motifs cannot be synthesized by nucleophilic substitution of alkylsulfonates with [ 18 F]KF-K 222 , and current synthetic methodologies are limited in scope. 9,27 We wondered whether our fluorination reaction could be a suitable methodology for the synthesis of [ 18 F] tertiary allylic fluorides. The initial experiments were performed with α-methylstyrene, reagent 2a , Rh 2 (esp) 2 , and [ 18 F]KF-K 222 (∼0.2 GBq).…”

Section: Resultsmentioning

confidence: 99%

Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters

et al. 2022

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“…Use of Olah’s reagent led to a clear fluoride formation (Entry 9), proving to be a suitable system for silyl fluoride synthesis (that can be later PET-activated by isotope exchange)), but it will be unlikely to transfer this fluorination condition into a direct radiofluorination method. Nevertheless, starting from this observation, radiofluorination conditions using the recently published iron-trapped [ 18 F]F species might be applicable (Verhoog et al 2019 ).…”

Section: Resultsmentioning

confidence: 99%

Fluorination of silyl prosthetic groups by fluorine mediated silyl ether linker cleavage: a concept study with conditions applicable in radiofluorination

Kramer

Greiner

Kopka

et al. 2022

EJNMMI radiopharm. chem.

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Background Positron emission tomography (PET) is a powerful tool in medical imaging, especially in combination with the PET radionuclide fluorine-18 that possesses optimal characteristics. For labelling of biomolecules and low-molecular weight tracers, fluorine-18 can be covalently bound to silicon by either nucleophilic replacements of leaving groups (like ethers) or by isotope exchange of fluorine-19. While nucleophilic substitutions require additional purification steps for the removal of contaminants, isotope exchange with fluorine-18 results in low molar activity. Both challenges can be addressed with a detagging-fluorination of an immobilized silyl ether motif. Results By overcoming the susceptibility towards hydrolysis, optimized detagging conditions (improved reaction time, fluorination reagent, linker, and resin) could afford the highly sterically hindered silyl fluoride motifs, that are commonly applied in radiochemistry in small and semipreparative scales. The described reaction conditions with fluorine-19 are transferrable to conditions with [18F]fluoride and silyl fluorides were obtained after approx. 10 min reaction time and in high-purity after mechanical filtration. Conclusions We present a proof-of-concept study for a detagging-fluorination of two silyl ethers that are bound to an optimized amino alcohol resin. We show with our model substrate that our solid-phase linker combination is capable of yielding the desired silicon fluoride in amounts sufficient for biological studies in animals or humans under standard fluorination conditions that may also be transferred to a radiolabelling setting. In conclusion, our presented approach could optimize the molar activity and simplify the preparation of radiofluorinated silyl fluorides.

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Ring opening of epoxides with [¹⁸F]FeF species to produce [¹⁸F]fluorohydrin PET imaging agents

Cited by 14 publications

References 46 publications

Closing the gap between 19F and 18F chemistry

Closing the gap between 19F and 18F chemistry

Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters

Fluorination of silyl prosthetic groups by fluorine mediated silyl ether linker cleavage: a concept study with conditions applicable in radiofluorination

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Ring opening of epoxides with [18F]FeF species to produce [18F]fluorohydrin PET imaging agents

Cited by 14 publications

References 46 publications

Closing the gap between 19F and 18F chemistry

Closing the gap between 19F and 18F chemistry

Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters

Fluorination of silyl prosthetic groups by fluorine mediated silyl ether linker cleavage: a concept study with conditions applicable in radiofluorination

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Ring opening of epoxides with [¹⁸F]FeF species to produce [¹⁸F]fluorohydrin PET imaging agents