Nucleophilic F-18-Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors: Advantages and Disadvantages

The field of labeling electron-rich aryl compounds with nucleophilic [F-18] fluoride has recently expanded with radio-fluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically di...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2017; no. 3; pp. 453 - 458
Main Authors Petersen, Ida Nymann, Kristensen, Jesper Langgaard, Herth, Matthias Manfred
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.01.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESIGN
RADIOFLUORINATION
ARENES
F-18-FLUORINATION
FLUORINATION
SALTS
FLUORIDE
POSITRON-EMISSION-TOMOGRAPHY
ARYL HALIDES
Comparative studies
Nucleophilic substitution
Spiro compounds
Ylides
BORYLATION
Isotopic labeling
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Summary:The field of labeling electron-rich aryl compounds with nucleophilic [F-18] fluoride has recently expanded with radio-fluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201601448