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Issue 1, 2014
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Mechanism of electrophilic fluorination with Pd(iv): fluoride capture and subsequent oxidative fluoride transfer

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Abstract

Electrophilic fluorinating reagents derived from fluoride are desirable for the synthesis of 18F-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 18F 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 18F PET imaging.

Graphical abstract: Mechanism of electrophilic fluorination with Pd(iv): fluoride capture and subsequent oxidative fluoride transfer

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The article was received on 23 Aug 2013, accepted on 16 Oct 2013 and first published on 31 Oct 2013


Article type: Edge Article
DOI: 10.1039/C3SC52367E
Chem. Sci., 2014,5, 169-179

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    Mechanism of electrophilic fluorination with Pd(IV): fluoride capture and subsequent oxidative fluoride transfer

    J. R. Brandt, E. Lee, G. B. Boursalian and T. Ritter, Chem. Sci., 2014, 5, 169
    DOI: 10.1039/C3SC52367E

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