In this project, we have investigated the synthesis of triazaborolopyridinium fluoride dyes such as 1  and 2   starting from   the 2-hydrazinylpyridine ligand and the appropriate boron-containing starting material.  Formation of these dyes has been confirmed using conventional characterization means including NMR spectroscopy and single crystal X-ray diffraction.  Motivated by the possible use of these dyes in [18F]-positron emission tomography, we have decided to determine if the B-F bonds of these compounds could be activated to allow for the subsequent incorporation of a radioactive 18F fluoride anion.  With this objective in mind, we found that 1  reacts with TMSOTf in the presence of (4-dimethylaminopyridine) to afford the boronium 3  + as the B-F bond activation product.  We are currently exploring the reactivity of 3  + with fluoride in order to simulate the introduction of [18F]-fluoride

B-F bond activation of triazaborolopyridinium fluoride dyes

243rd National Meeting (2012)

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