Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones

A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted b...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-10, Vol.56 (42), p.13006-13010
Main Authors: Narayanam, Maruthi Kumar, Ma, Gaoyuan, Champagne, Pier Alexandre, Houk, Kendall N., Murphy, Jennifer M.
Format: Article
Language:English
Subjects:
Aniline
click chemistry
Fluoridation
Fluorides
Fluorine Radioisotopes - chemistry
fluorine-18
fluoroarene
Intermediates
Isotope Labeling
Molecular Conformation
Neuropeptides - chemistry
peptide radiolabeling
Positron-Emission Tomography
Radiopharmaceuticals - chemical synthesis
sydnone
Sydnones - chemistry
Thermodynamics
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Description
Summary:A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F‐labeled neuropeptide. Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N‐arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F‐labeling of peptides.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201707274