6533b822fe1ef96bd127d52d
RESEARCH PRODUCT
No carrier-added nucleophilic aromatic radiofluorination using solid phase supported arenediazonium sulfonates and 1-(aryldiazenyl)piperazines
Patrick J. RissSonja KuschelSonja KuschelFranklin I. Aigbirhiosubject
Organic ChemistryThermal decompositionBiochemistryPiperazinechemistry.chemical_compoundSulfonatechemistryNucleophileCovalent bondDrug DiscoveryPolymer chemistryOrganic chemistryBalz–Schiemann reactionIon-exchange resinFluoridedescription
Abstract This Letter concerns the investigation of a solid phase based method for no carrier-added nucleophilic [ 18 F]fluorination of aromatic compounds via de-diazofluorination. Initial screening of reaction conditions was conducted using soluble analogues, that is, substituted benzenediazonium tosylates and 1-(phenyldiazenyl)piperazines in solution. This was followed by translation of the principle conditions to solid phase bound analogues. A variety of substituted aryldiazonium cations were immobilised using a sulfonate functionalised ion exchange resin and labelled with [ 18 F]fluoride ion by Balz–Schiemann like thermal decomposition in the presence of no carrier-added [ 18 F]fluoride ion. Likewise, a chloromethyl-bearing (Merrifield-) resin was modified using piperazine to provide the means for covalent immobilisation of diazonium ions. The resin bound 1-(aryldiazenyl)piperazines obtained were used as substrates for a Wallach reaction with hydrogen [ 18 F]fluoride.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-04-01 | Tetrahedron Letters |