Oxidation of aromatic lithium thiolates into sulfinate salts: an attractive entry to aryl sulfones labeled with carbon-11.
[reaction: see text] Aromatic 11C-sulfones were synthesized by S alkylation of lithium arenesulfinates, which are readily available from the corresponding thiols by an oxaziridine-mediated oxidation reaction with [11C]alkyl iodides in THF/H2O (4:1) at 150 degrees C. The radiosyntheses, including purification by HPLC, were completed in an average of 35 min from the end of the bombardment with 55-76% overall radiochemical yields (decay corrected). The described procedure extends the range of accessible labeling methods.
Martin
Claudie
C
Laboratoire de Chimie Moléculaire et Thio-Organique (UMR CNRS 6507), ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, F-14050 Caen, France.
Sandrinelli
Franck
F
Perrio
Cécile
C
Perrio
Stéphane
S
Lasne
Marie-Claire
MC
D002250:Carbon Radioisotopes / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012492:Salts / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D002250:Carbon Radioisotopes; D006847:Hydrocarbons, Iodinated; D012492:Salts; D013438:Sulfhydryl Compounds; D013450:Sulfones; D013455:Sulfur; D008094:Lithium; C014055:methyl iodide