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Direct n.c.a. radioiodination of weakly activated arenes using metal salts

  • E. Mennicke , M.H. Holschbach and Heinz H. Coenen
Published/Copyright: September 25, 2009
Radiochimica Acta
From the journal Radiochimica Acta Volume 88 Issue 3-4

The direct electrophilic no-carrier-added (n.c.a.) aromatic radioiodination was examined using various metal salts in trifluoroacetic acid (TFA) as in situ oxidation agents. Two different types of metal salts were used comprising TFA-soluble (Pb(CH3CO2)4, Mn(CH3CO2)3, KMnO4, Tl(CF3CO2)3, AgCF3SO3) and TFA-insoluble (Ce(CF3SO3)4, RuCl3, FeBr3, K2Cr2O7) salts. Optimization of both labelling systems has been performed using Pb(CH3CO2) 4, Ce(CF3SO3) 4 and benzene as a model substrate. At room temperature, the one-pot synthesis was completed within 15 min, resulting in a radiochemical yield of 82% and 64% using Pb(CH3CO2)4 and Ce(CF3SO3)4, respectively. Radioiodination of weakly activated monosubstituted benzene derivatives led to high radiochemical yields of about 80% and 60% of the corresponding ortho- and para-radioiodo-isomers using both salts. Weakly deactivated chlorobenzene could only be radioiodinated with Ce(CF3SO3)4 as oxidant, forming exclusively the para-product with a radiochemical yield of about 35%. Using the optimized reaction parameters for the other TFA-soluble and -insoluble metal salts with benzene and toluene good radiochemical yields were obtained in all cases except for the manganese and silver salts. Apparently their oxidation power was not strong enough for the radioiodination of the non-activated benzenes. In situ formed trifluoroacetyl [131I]hypoiodite is discussed with regard to the reaction mechanism.

Published Online: 2009-9-25
Published in Print: 2000-3-1

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  15. Doppler broadening as a probe of the chemical environment following oxygen-14 decay
  16. In-target chemistry during the production of 15O and 11C using 3He reactions
  17. 11C-methane production in small volume, high pressure gas targets
  18. 11C-methylations using 11C-methyl iodide and tetrabutylammonium fluoride
  19. Specific activity of [11C]CO2 generated in a N2 gas target: effect of irradiation dose, irradiation history, oxygen content and beam energy
  20. Effect of dissolved gas on the specific activity of N-13 labeled ions generated in water by the 16O(p,α)13N reaction
  21. Direct n.c.a. radioiodination of weakly activated arenes using metal salts
  22. Synthesis of substituted [123I]imidazo[1,2-α]pyridines as potential probes for the study of the peripheral benzodiazepine receptors using SPECT
  23. Determination of trace impurities in iron-based alloy using neutron activation analysis
  24. EXAFS analyses of technetium(I) carbonyl complexes – stability studies in solutions
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https://doi.org/10.1524/ract.2000.88.3-4.221

Articles in the same Issue

  1. Preface: Alfred P. Wolf Memorial Issue
  2. Im Memoriam Alfred P. Wolf
  3. The centenary of a controversial discovery: actinium
  4. Proton-induced nuclear reactions in neptunium-237 targets. Production of plutonium tracers in the energy range 15-40 MeV
  5. Possibility of production of 81Rb via the 80Kr(d,n) reaction at a small cyclotron
  6. Positron emission intensity in the decay of 120gI
  7. Production of high specific activity 27Mg by fast neutron irradiation and recoil-aided leaching
  8. Production of strontium-82 for the Cardiogen® PET generator: a project of the Department of Energy Virtual Isotope Center
  9. Lutetium-177-EDTMP for bone pain palliation. Preparation, biodistribution and pre-clinical studies
  10. Thermochromatographic separation of no-carrier-added 186Re or 188Re from tungsten targets relevant to nuclear medical applications
  11. Low energy cyclotron production and chemical separation of "no carrier added" iodine-124 from a reusable, enriched tellurium-124 dioxide/aluminum oxide solid solution target
  12. Physicochemical and radiochemical aspects of separation of radioiodine from TeO2-targets
  13. Novel separation of thallium-201 using p-tert-butylcalix[4]arene derivative
  14. Recovery of 201Tl by ion exchange chromatography from proton bombarded thallium cyclotron targets
  15. Doppler broadening as a probe of the chemical environment following oxygen-14 decay
  16. In-target chemistry during the production of 15O and 11C using 3He reactions
  17. 11C-methane production in small volume, high pressure gas targets
  18. 11C-methylations using 11C-methyl iodide and tetrabutylammonium fluoride
  19. Specific activity of [11C]CO2 generated in a N2 gas target: effect of irradiation dose, irradiation history, oxygen content and beam energy
  20. Effect of dissolved gas on the specific activity of N-13 labeled ions generated in water by the 16O(p,α)13N reaction
  21. Direct n.c.a. radioiodination of weakly activated arenes using metal salts
  22. Synthesis of substituted [123I]imidazo[1,2-α]pyridines as potential probes for the study of the peripheral benzodiazepine receptors using SPECT
  23. Determination of trace impurities in iron-based alloy using neutron activation analysis
  24. EXAFS analyses of technetium(I) carbonyl complexes – stability studies in solutions
  25. Syntheses and structures of technetium(V) and rhenium(V) oxo complexes of peptide having KYC-sequence
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