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Automated Radiochemical Synthesis of [18F]3F4AP: A Novel PET Tracer for Imaging Demyelinating Diseases
Published on: May 29, 2017
Synthesis of Dideuterofluoroarene 3ΔF(D)-NMR Reporter-Resolvers for Structural, Mechanistic, and Kinetic Studies
Pedro H Helou de Oliveira1, Róisín O'Dea1, Andrés García-Domínguez1
1School of Chemistry, University of Edinburgh, Joseph Black Building, Edinburgh EH9 3FJ, United Kingdom.
Abstract:
3,5-Dideutero-4-fluorophenyl compounds are generated by ipso-functionalization of (4-fluorophenyl)trimethylsilane-d2, prepared in >99 atom % isotopic purity, on a multigram scale, by selective H/D exchange at the C-H sites, ortho to fluorine, using a Lochmann-Schlosser superbase and MeOD. The 3,5-dideutero-4-fluorophenyl "reporter-resolver" system has an isotope shift, ΔδF, in the range of 0.5 to 0.6 ppm. It enables in situ 19F NMR spectroscopic reaction monitoring of crossover, entrainment, ratiometric heavy atom KIEs, and unambiguous structural assignments and integrations via three NMR-active nuclei.
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