2020
DOI: 10.21203/rs.3.rs-111390/v1
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Arene Radiofluorination Enabled by Photoredox-Mediated Halide Interconversion

Abstract: Positron emission tomography (PET) is a powerful imaging technology that could visualize and measure metabolic processes in vivo and/or obtain unique information about drug candidates at early stages. Identification of new and improved molecular probes plays a critical role in PET, but its progress is limited in many situations due to the lack of efficient and simple labeling methods to modify biologically active small molecules and/or drugs. Although various approaches have been reported, current methods to r… Show more

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Cited by 3 publications
(7 citation statements)
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“…Nicewicz and co-workers have demonstrated the wide applications of acridinium photoredox catalysts in cation-radical acceleratednucleophilic aromatic substitutions (CRA-S N Ar) via single electron oxidation of electron-rich arenes. [14] Similar aromatic radical cation intermediates were also used to form high energy alkoxy radical species integrating proton-coupled electron transfer (PCET) for CÀ C bond cleavage. [24] While powerful for these alternative reactions, such competing outerspheric electron transfer processes render the generation of the key carboxylic radical needed for decarboxylation inefficient in the presence of electron-rich arenes (Figure 3).…”
Section: Resultsmentioning
confidence: 99%
“…Nicewicz and co-workers have demonstrated the wide applications of acridinium photoredox catalysts in cation-radical acceleratednucleophilic aromatic substitutions (CRA-S N Ar) via single electron oxidation of electron-rich arenes. [14] Similar aromatic radical cation intermediates were also used to form high energy alkoxy radical species integrating proton-coupled electron transfer (PCET) for CÀ C bond cleavage. [24] While powerful for these alternative reactions, such competing outerspheric electron transfer processes render the generation of the key carboxylic radical needed for decarboxylation inefficient in the presence of electron-rich arenes (Figure 3).…”
Section: Resultsmentioning
confidence: 99%
“…The labeling protocol was modified from the literature . In a 2 mL Eppendorf tube, compound 4a (500 nmol) was mixed with 50 μL of target water (containing about 25 to 30 mCi 18 F fluoride, which was prepared by 18 O (p,n) 18 F using cyclotron).…”
Section: Methodsmentioning
confidence: 99%
“…1 H NMR (400 MHz, acetone-d 6 ) δ 7.21 (d, J = 8.0 Hz, 2H), 6.85 (d, J = 8.1 Hz, 2H), 6.74−6.17 (m, 3H), 3.77 (s, 3H), 2.58 (dd, J = 47.0, 32.6 Hz, 2H). 13 16 In a 2 mL Eppendorf tube, compound 4a (500 nmol) was mixed with 50 μL of target water (containing about 25 to 30 mCi 18 F fluoride, which was prepared by 18 O (p,n) 18 F using cyclotron). Then, the reaction was heated at 85 °C for 15 min, quenched with 1 mL of deionized water (containing 0.1% TFA), and separated by semi-preparative HPLC.…”
Section: Methodsmentioning
confidence: 99%
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