[18F]CuCF3: A [18F]Trifluoromethylating Agent for Arylboronic Acids and Aryl Iodides

Positron emission tomography has emerged as the leading method for medical imaging with fluorine‐18 as the most widely used radioactive isotope. Here we report a semi‐automated method for the preparation of valuable [18F]trifluoromethylcopper, as well as its use for the radiosynthesis of [18F]triflu...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-07, Vol.20 (31), p.9514-9518
Main Authors: Ivashkin, Pavel, Lemonnier, Gérald, Cousin, Jonathan, Grégoire, Vincent, Labar, Daniel, Jubault, Philippe, Pannecoucke, Xavier
Format: Article
Language:English
Subjects:
Acids
Alkylating Agents - chemistry
Analytical chemistry
arylboronic acid
Boronic Acids - chemical synthesis
Catalysis
Chemical Sciences
Cheminformatics
Chemistry
Chlorofluorocarbons, Methane - chemistry
copper
Copper - chemistry
Crystallography, X-Ray
fluorine
Fluorine Radioisotopes - chemistry
Hydrocarbons, Iodinated - chemical synthesis
Hydrocarbons, Iodinated - chemistry
Isotope Labeling - methods
Medicinal Chemistry
Methylation
Models, Molecular
Molecular Structure
or physical chemistry
Organic chemistry
Organometallic Compounds - chemical synthesis
Positron-Emission Tomography - methods
Radioactive materials
radiochemistry
Radiopharmaceuticals - chemical synthesis
Theoretical and
trifluoromethylation
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Summary:Positron emission tomography has emerged as the leading method for medical imaging with fluorine‐18 as the most widely used radioactive isotope. Here we report a semi‐automated method for the preparation of valuable [18F]trifluoromethylcopper, as well as its use for the radiosynthesis of [18F]trifluoromethylarenes and heteroarenes. Mild conditions of [18F]trifluoromethylation make this method particularly useful for the radiosynthesis of pharmacologically relevant [18F]trifluoromethylarenes and heteroarenes. 18F Radiochemistry: A semi‐automated method for the fast preparation of radiolabelled (trifluoromethyl)copper is reported (see scheme), thus making [18F]CuCF3 almost as accessible as [18F]fluoride itself for the preparation of radiolabelled trifluoromethylated probes. It can be used for the preparation of radiolabelled trifluoromethylarenes from arylboronic acids and aryliodides. This methodology is clean, efficient and consistent with the specific requirements of radiochemistry.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403630