A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging

Lee, Eunsung; Kamlet, Adam S.; Powers, Dennis A.; Neumann, Constanze N.; Boursalian, Gregory B.; Furuya, Takeru; Choi, Daniel; Hooker, Jacob M.; Ritter, Tobias

doi:10.1126/science.1212625

Cited by 387 publications

(268 citation statements)

References 28 publications

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“…In 2013, Mazzotti et al developed palladium-III -catalyzed fluorination of aryl boronic acids ( Figure 5). 21 Unlike the previously reported Pd-mediated fluorination, 13,19 the C-F bond formation presented here seems to proceed without the formation of organopalladium complexes. The author proposed a single-electron-transfer (SET) mechanism involving a well-defined Pd III 3 .…”

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confidence: 41%

“…35 This reaction was an analog to the Chichibabin reaction and can be adopted for a broad range of substituted nitrogen heterocycles. During the course of the reaction, AgF 2 is consumed, while yellow solid AgF is formed and could be observed by 19 …”

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confidence: 99%

“…19 Treatment of the reagent (a Pd IV complex) with potassium fluoride (KF) affords a new Pd IV -F complex within 5 minutes, which could further react with Ar-Pd complex to give the corresponding Ar-F in 10 minutes. It should be noted that during this transformation, a net [ 18 F]-fluoride umpolung is realized.…”

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confidence: 99%

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Recent advances in green fluorine chemistry

Zeng¹,

Hu²

2015

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Recent advances in green fluorine chemistry

Zeng¹,

Hu²

2015

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“…Fluorination increases the therapeutic efficacy or pharmacokinetic behaviour of numerous drugs 18,19 , improves the stability of proteins without altering their structures and functions 21 , and allows the detection or imaging of the labelled compounds using magnetic resonance imaging or positron emission tomography imaging 23,24 . Fluorinated compounds are both hydrophobic and lipophobic, and have a high phase-separation tendency in both polar and non-polar environments 25,26 .…”

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A fluorinated dendrimer achieves excellent gene transfection efficacy at extremely low nitrogen to phosphorus ratios

et al. 2014

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Polymers have shown great promise in the design of high efficient and low cytotoxic gene vectors. Here we synthesize fluorinated dendrimers for use as gene vectors. Fluorinated dendrimers achieve excellent gene transfection efficacy in several cell lines (higher than 90% in HEK293 and HeLa cells) at extremely low N/P ratios. These polymers show superior efficacy and biocompatibility compared with several commercial transfection reagents such as Lipofectamine 2000 and SuperFect. Fluorination enhances the cellular uptake of the dendrimer/DNA polyplexes and facilitates their endosomal escape. In addition, the fluorinated dendrimer shows excellent serum resistance and exhibits high gene transfection efficacy even in medium containing 50% FBS. The results suggest that fluorinated dendrimers are a new class of highly efficient gene vectors and fluorination is a promising strategy to design gene vectors without involving sophisticated syntheses.

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“…1 An alternative, non-metal based strategy could be envisaged using cyclic hypervalent iodine(III) 15 compounds which have been shown to be mild, non-toxic and selective reagents for halogenation. [2][3][4] These reagents are normally prepared by oxidation of iodine(I) species with electrophilic reagents such as tert-butyl hypochlorite (1 → 3) and N-bromosuccinimide (1 → 2), 2 Our research group is interested in designing new methods for introducing fluorine into organic molecules 5 because of the importance of incorporating fluorine into drug candidate 35 molecules.…”

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Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride

et al. 2013

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The air and moisture stable fluoroiodane 8, readily prepared on a 6 g scale by nucleophilic fluorination of the hydroxyiodane 7 with TREAT-HF, has been used as an electrophilic fluorinating reagent for the first time to monofluorinate 1,3-ketoesters and difluorinate 1,3-diketones 10 in good isolated yields.In late 2011, Ritter reported the first electrophilic fluorination using the fluoride anion in a transfer fluorination between two palladium species. 1 An alternative, non-metal based strategy could be envisaged using cyclic hypervalent iodine(III) 15 compounds which have been shown to be mild, non-toxic and selective reagents for halogenation. Our research group is interested in designing new methods for introducing fluorine into organic molecules 5 because of the importance of incorporating fluorine into drug candidate 35 molecules. 6 Since Banks first reported SelectFluor in 1992, 7 the fluoraza reagents have become increasingly popular electrophilic fluorinating reagents because they are commercially-available, shelf-stable powders that can be used to fluorinate a wide variety of substrates. 8 The main disadvantage of these electrophilic 40 fluorinating reagents, however, is that they are very expensive because they are normally made from elemental fluorine. ____________________________________________________ Alternative reagents such as (difluoroiodo)arenes have been prepared from aqueous HF, but they are extremely moisture sensitive and are commonly used as a freshly prepared solution, without isolation, or they can be generated in situ. 9 Inspired by Togni's seminal work on electrophilic trifluoromethylation, 3 we 55 were interested in developing a new class of stable fluorinating reagents based on the cyclic hypervalent iodine(III) skeleton, but generated from cheap sources of fluoride. Here, we will report three different methods for the preparation of an air and moisture stable fluorinated hypervalent iodine reagent 8 and preliminary 60 results on its' fluorination of a series of 1,3-dicarbonyl substrates.Scheme 2 Synthesis of the fluoroiodane 8 using TREAT-HF

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A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging

Abstract: A palladium compound facilitates rapid incorporation of radioactive fluoride into prospective tracers for medical imaging.

Cited by 387 publications

References 28 publications

Recent advances in green fluorine chemistry

Recent advances in green fluorine chemistry

A fluorinated dendrimer achieves excellent gene transfection efficacy at extremely low nitrogen to phosphorus ratios

Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride

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