期刊
CHEMICAL SCIENCE
卷 5, 期 1, 页码 169-179出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc52367e
关键词
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资金
- NIH-NIGMS [GM088237]
- IH-NIBIB [EB013042-02]
- NSF GRFP [DGE0644491]
Electrophilic fluorinating reagents derived from fluoride are desirable for the synthesis of F-18-labeled molecules for positron emission tomography (PET). Here, we study the mechanism by which a Pd(IV)complex captures fluoride and subsequently transfers it to nucleophiles. The intermediate Pd(IV)-F is formed with high rates even at the nano-to micromolar fluoride concentrations typical for radiosyntheses with F-18 due to fast formation of an outer-sphere complex between fluoride and Pd(IV). The subsequent fluorine transfer from the Pd(IV)-F complex is proposed to proceed through an unusual SET/fluoride transfer/SET mechanism. The findings detailed in this manuscript provide a theoretical foundation suitable for addressing a more general approach for electrophilic fluorination with high specific activity F-18 PET imaging.
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