<sup>18</sup>F‐Radiolabeling of Aromatic Compounds Using Triarylsulfonium Salts

Mu, Linjing; Fischer, Cindy R.; Holland, Jason P.; Becaud, Jessica; Schubiger, P. August; Schibli, Roger; Ametamey, Simon M.; Graham, Keith; Stellfeld, Timo; Dinkelborg, Ludger; Lehmann, Lutz

doi:10.1002/ejoc.201101730

Cited by 83 publications

(62 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Other efforts to achieve this goal include applications of triarylsulphonium salts 9 , diarylsulphoxides 10 or the post-S N Ar conversion of activating, electron-withdrawing groups into electron-donating groups, for example, through Baeyer-Villiger oxidation 11 , all of which are based on reactions towards electron-deficient arenes and have limited substrate scope. Alternatively, transition-metal-mediated fluorination reactions (Fig.…”

mentioning

confidence: 99%

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

et al. 2014

View full text Add to dashboard Cite

Fluorine-18 (t ½ ¼ 109.7 min) is the most commonly used isotope to prepare radiopharmaceuticals for molecular imaging by positron emission tomography (PET). Nucleophilic aromatic substitution reactions of suitably activated (electron-deficient) aromatic substrates with no-carrier-added [ 18 F]fluoride ion are routinely carried out in the synthesis of radiotracers in high specific activities. Despite extensive efforts to develop a general 18 F-labelling technique for non-activated arenes there is an urgent and unmet need to achieve this goal. Here we describe an effective solution that relies on the chemistry of spirocyclic hypervalent iodine(III) complexes, which serve as precursors for rapid, one-step regioselective radiofluorination with [ 18 F]fluoride. This methodology proves to be efficient for radiolabelling a diverse range of non-activated functionalized arenes and heteroarenes, including arene substrates bearing electron-donating groups, bulky ortho functionalities, benzylic substituents and meta-substituted electron-withdrawing groups. Polyfunctional molecules and a range of previously elusive 18 F-labelled building blocks, compounds and radiopharmaceuticals are synthesized.

show abstract

mentioning

confidence: 99%

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

et al. 2014

View full text Add to dashboard Cite

show abstract

“…[4] Trimethylanilinium triflates, triarylsulfonium salts, [8] diarylsulfoxides, [9] and diarylselenones [10] are typical precursors used in S N Ar reactions (Scheme 1). Diaryliodonium salts [11] are also viable precursors which give moderate to good selectivity that can be significantly improved with a copper catalyst.…”

mentioning

confidence: 99%

Synthesis of [¹⁸F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones

Narayanam

Champagne

et al. 2017

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

“…The product was isolated as colorless oil (0.09 g, 80% (24). Compound 21 (0.1 g, 0.27 mmol) was dissolved in methanol (0.5 ml) and THF (0.5 ml).…”

Section: -(4-benzhydrylpiperazin-1-yl)-2-fluorobutan-1-ol Dihydrochlmentioning

confidence: 99%

Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography

et al. 2015

View full text Add to dashboard Cite

Increased activity of efflux transporters, e.g., P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), at the blood-brain barrier is a pathological hallmark of many neurological diseases, and the resulting multiple drug resistance represents a major clinical challenge. Noninvasive imaging of transporter activity can help to clarify the underlying mechanisms of drug resistance and facilitate diagnosis, patient stratification, and treatment monitoring. We have developed a metabolically activated radiotracer for functional imaging of P-gp/BCRP activity with positron emission tomography (PET). In preclinical studies, the tracer showed excellent initial brain uptake and clean conversion to the desired metabolite, although at a sluggish rate. Blocking with P-gp/BCRP modulators led to increased levels of brain radioactivity; however, dynamic PET did not show differential clearance rates between treatment and control groups. Our results provide proof-of-concept for development of prodrug tracers for imaging of P-gp/BCRP function in vivo but also highlight some challenges associated with this strategy.

show abstract

¹⁸F‐Radiolabeling of Aromatic Compounds Using Triarylsulfonium Salts

Cited by 83 publications

References 17 publications

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Synthesis of [¹⁸F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones

Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography

Contact Info

Product

Resources

About

18F‐Radiolabeling of Aromatic Compounds Using Triarylsulfonium Salts

Cited by 83 publications

References 17 publications

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones

Development of Fluorine-18 Labeled Metabolically Activated Tracers for Imaging of Drug Efflux Transporters with Positron Emission Tomography

Contact Info

Product

Resources

About

¹⁸F‐Radiolabeling of Aromatic Compounds Using Triarylsulfonium Salts

Synthesis of [¹⁸F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones