ArticleOrganic & biomolecular chemistry2013
Single-step syntheses of no-carrier-added functionalized [18F]fluoroarenes as labeling synthons from diaryliodonium salts.
Article in Organic & biomolecular chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- PET Molecular Imaging in Drug Development: The Imaging and Chemistry Perspective.Frontiers in medicine · 2022Review
- Rapid synthesis of maleimide functionalized fluorine-18 labeled prosthetic group using "radio-fluorination on the Sep-Pak" method.Journal of labelled compounds & radiopharmaceuticals · 2018Article
- Hypervalent aryliodine compounds as precursors for radiofluorination.Journal of labelled compounds & radiopharmaceuticals · 2018Review
- Article
- Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors.Journal of labelled compounds & radiopharmaceuticals · 2017Article
- Crystal Structures of Diaryliodonium Fluorides and Their Implications for Fluorination Mechanisms.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines.Angewandte Chemie (International ed. in English) · 2016Article
- Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [(18)F]Fluoroarenes from Cyclotron-Produced [(18)F]Fluoride Ion.The Journal of organic chemistry · 2016Article
- A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.European journal of organic chemistry · 2015Article
- Fluorine-18 radiochemistry, labeling strategies and synthetic routes.Bioconjugate chemistry · 2015Review
- Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts.Organic letters · 2014Article
- 18F-labelled intermediates for radiosynthesis by modular build-up reactions: newer developments.BioMed research international · 2014Review
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2 authors.
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Abstract
Radiotracers labelled with short-lived fluorine-18 (t(1/2) = 109.7 min) are keenly sought for biomedical imaging with positron emission tomography (PET). The radiotracers are mostly required at high specific radioactivities, necessitating their radiosyntheses from cyclotron-produced no-carrier-added [(18)F]fluoride ion. PET radiotracers encompass wide structural diversity and molecular weight. Hence, diverse (18)F-labeling methodology is needed to accomplish the required radiosyntheses in a simple and rapid manner. A useful strategy is to introduce nucleophilic [(18)F]fluoride ion first into a labeling synthon that may then be applied to label the target radiotracer. Here, we show that various functionalized [(18)F]fluoroarenes may be rapidly synthesized as labeling synthons through single-step reactions of appropriate diaryliodonium salts with [(18)F]fluoride ion. Decay-corrected radiochemical yields (RCYs) varied with position of functional group, choice of electron-rich aryl ring in the diaryliodonium salt, and choice of anion. Under best conditions, (18)F-labeled fluorobenzaldehydes, fluorobenzyl halides, fluorobenzoic acid esters and fluorophenyl ketones were obtained selectively in 40-73%, 20-55%, 46-89% and 81-98% RCYs, respectively. This versatile straightforward methodology will enhance the scope for producing structurally complex, yet useful, PET radiotracers.
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