One-step reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane


One-step reductive etherification of 4-[18F]fluoro-benzaldehyde with decaborane

Funke, U.; Jia, H.; Fischer, S.; Scheunemann, M.; Steinbach, J.

Reductive coulling reactions between 4-[18F]fluoro-benzaldehyde ([18F]19 and different alcoholsby use of decaborane (B10H14)as reducing agent have the potential to synthesize 4-[18F]fluoro-benzylethers in one step. [18F]1 was sythesized from 4-trimethylammonium benzaldehyde (triflate salt) via a standard fluorination procedure (K[18F]F/Kryprofix 222) in dimethylformamide at 90°C for 25 min and purified by solid-phase extraction. Subsequently, reductive etherifications of [18F]1 were performed as one-step reactions with primary and secondary alcohols, mediated by B10H14 in acetonitrile at 60°C. Various 4-[18F]fluorobenzyl ethers (6 examples are shown) were obtained within 1-2h reaction time in decay-corrected radiochemical yields of 12-45%.

Keywords: 4[18F]fluoro-benzylether; fluorine-18; reductive etherification; decarborane; labelling

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Publ.-Id: 8671