cationic boranes as attractive tools for radiochemistry with fluorine-18

ICHAC-XI, International Conference on Heteroatom Chemistry
Caen (France), 14-19 June 2015
CATIONIC BORANES AS ATTRACTIVE TOOLS FOR
RADIOCHEMISTRY WITH FLUORINE-18
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Sébastien Schmitt,1 Cécile Perrio,1* Kantapat Chansaenpak,2 François Gabbaï,2 Daniel Pla
Queral,3 Béatrice Mestre-Voegtle,3 Emmanuel Gras3
1
UMR 6301 ISTCT, LDM-TEP, CNRS, CEA, Université de Caen-Basse Normandie, GIP
CYCERON, Bd Henri Becquerel, BP 5229, 14074 Caen, France - perrio@cyceron.fr
2
Department of Chemistry, Texas A&M University, College Station, Texas, US
3
77843UPR 8241, Laboratoire de Chimie de Coordination, BP 44099, 205 Route de Narbonne,
31077 Toulouse cedex 4, France
Fluorine-18 (t1/2 = 110 min) is an essential short-lived radioisotope for the development
of radiopharmaceuticals for positron emission tomography (PET). The most commonly used
source of fluorine-18 is the [18F]fluoride anion obtained in aqueous solution. Under these
conditions, [18F]fluoride is strongly hydrated and unreactive for nucleophilic substitution. The
well-established procedure to increase its reactivity requires SPE and drying steps which are
time-consumming, complex for automation, and not suited for miniaturization.
Previous works by Gabbaï et al demonstrated the high potential of cationic boranes to
achieve phase transfer of fluoride according to an anion capture-release strategy.1 We
successfully adapted this strategy for the rapid conversion of aqueous [18F]fluoride to “organic”
[18F]fluoride usable for radiofluorination. The overall process will be detailed and discussed.
1
As typical references : Lee, M. H.; Agou, T.; Kobayashi, J.; Kawashima, T.; Gabbaï, F. P. Chem. Commun. 2007,
1133; Hudnall T. W; Gabbaï, F. P. J. Am. Chem. Soc. 2007, 129, 11978; Kim, Y.; Gabbaï, F. P. J. Am. Chem. Soc.
2009, 131, 3363.