Nickel-Mediated Oxidative Fluorination for PET with Aqueous [<sup>18</sup>F] Fluoride

Lee, Eunsung; Hooker, Jacob M.; Ritter, Tobias

doi:10.1021/ja3084797

Cited by 272 publications

(301 citation statements)

References 23 publications

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“…As shown in Fig. 4, a N (37), previously prepared by transition-metal-mediated methods 12,13 , was also synthesized, in 23% incorporation yield (Supplementary Fig. 20).…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2014

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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.

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“…As shown in Fig. 4, a N (37), previously prepared by transition-metal-mediated methods 12,13 , was also synthesized, in 23% incorporation yield (Supplementary Fig. 20).…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2014

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“…In the case of radiofluorine 18 F, electron-demanding ethyl benzoates were applied [24,25] and the fluorine was introduced via a nucleophilic substitution S N Ar of the trimethylammonium group in most of the cases [2]. Newer developments are developments are based on the use of iodonium salts [26,27] or nickel complexes [28] as precursors. Afterwards, the ethyl group was cleaved followed by the introduction of the succinimidyl group.…”

Section: Synthesis and Chemistrymentioning

confidence: 99%

“…Crystals 2017, 7, 90 2 of 8 developments are based on the use of iodonium salts [26,27] or nickel complexes [28] as precursors. Afterwards, the ethyl group was cleaved followed by the introduction of the succinimidyl group.…”

Section: X-ray Structure Determinationmentioning

confidence: 99%

X-ray Structures of Succinimidyl Halobenzoates

2017

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Abstract:The crystal and molecular structures of five succinimidyl halobenzoates are reported. Corresponding derivatives with the respective halo-radionuclide ( 18 F, 76 Br, 123 I/ 124 I/ 125 I/ 131 I) were prepared and used for the radiolabeling of biologically active (macro-)molecules (peptides, proteins, antibodies) under mild labeling conditions. All compounds were crystalized from petroleum ether/ethyl acetate mixtures.

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“…The oxidative fluorination of pre-functionalized aryl metal complexes has been developed by several groups and has especially been successful for radiofluorination with [ 18 F]fluoride. In 2012, the Ritter group reported that arylnickel(II) complexes could be used for the regioselective synthesis of aryl fluorides, with a combination of a fluoride source such at TBAT and hypervalent iodine oxidant 13 [179]. The nickel-mediated oxidative fluorination reaction enabled a one-step radiofluorination of arylnickel(II) complexes (synthesized by oxidative addition of an aryl halide to a Ni(0) precursor) using aqueous [ 18 F] fluoride and oxidant 13 (Fig.…”

Section: Oxidative Arene Fluorination With Fluoridementioning

confidence: 99%

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Campbell

Hoover

Ritter

2014

Topics in Organometallic Chemistry

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The development of new C-F bond forming reactions from organotransition metal complexes has played a key role in advancing the field of fluorination chemistry and has allowed for improved access to fluorinated organic molecules of interest in medicine, materials, and agrochemicals. In this review, we describe the development of transition metal-mediated and metal-catalyzed fluorination methods over the past decade. Special attention is paid to the variety of organometallic mechanisms by which C-F bond formation can occur and the strengths and limitations of different approaches.

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Nickel-Mediated Oxidative Fluorination for PET with Aqueous [¹⁸F] Fluoride

Abstract: A one-step oxidative fluorination for carbon–fluorine bond formation from well-defined nickel complexes with oxidant and aqueous fluoride is presented, which enables a straightforward and practical 18F late-stage fluorination of complex small molecules with potential for PET imaging.

Cited by 272 publications

References 23 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

X-ray Structures of Succinimidyl Halobenzoates

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

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Nickel-Mediated Oxidative Fluorination for PET with Aqueous [18F] Fluoride

Abstract: A one-step oxidative fluorination for carbon–fluorine bond formation from well-defined nickel complexes with oxidant and aqueous fluoride is presented, which enables a straightforward and practical 18F late-stage fluorination of complex small molecules with potential for PET imaging.

Cited by 272 publications

References 23 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

X-ray Structures of Succinimidyl Halobenzoates

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

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Product

Resources

About

Nickel-Mediated Oxidative Fluorination for PET with Aqueous [¹⁸F] Fluoride