Radiotracer-based positron emission tomography (PET) for qualitative and quantitative analysis in clinical oncology, neurology, and cardiovascular disorders is one of the most rapidly growing areas of non-invasive medical imaging. Therefore, there has become a need for new methodologies for the incorporation of radionuclides (18F, 11C, 13N) into organic molecules to broaden the existing toolbox of reactions for radiochemists. [18F] Fluorine has become of increased importance due to its low energy of positron emission and its relatively long half-life (t1/2 = 109.8 min). We have developed a transition-metal mediated nucleophilic [18F] fluorine substitution of allylic trichloroacetimdiates providing radiolabeled allylic fluorides in moderate to good radiochemical yields under ambient reaction conditions (25 °C and open to air). Importantly this reaction is tolerant of multiple functional groups including esters, ethers, and azides that could allow for further modification post labeling. Further, this methodology could be utilized in the radiolabeling of peptides via a thiol-ene cross coupling reaction. This would have the possibility to reduce the overall reaction times of current peptide labeling techniques while increasing the overall radiochemical yield.

Regioselective synthesis of [18F] allylic fluorides for PET imaging via iridium-mediated fluorination of trichloroacetimidates with [18F]KF-kryptofix

255th National Meeting (2018)

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