Labelling of fluorinated aromatics by isotopic exchange with [¹⁸F]fluoride

Abstract

fluoride-18F i o n i n aromatic r i n g s i s r e p o r t e d h e r e u t i l i z i n g rubidium-18F-fluoride i n ' DMSO on model compounds. a c t i v i t i e s i n t h e 3 x LO4 Ci/mol r e g i o n a r e r e a d i l y a c h i e v a b l e . Nucleophilic s u b s t i t u t i o n i s shown t o b e an a t t r a c t i v e modality

[18F]/19F exchange in fluorine containing compounds for potential use in 18F‐labelling strategies

“…14 The replacement of a hydrogen atom by a fluorine atom can alter the pK a , dipole moment, lipophilicity, hydrogen-bonding properties, or chemical reactivity. 15 Halogen exchange is well known, 16,17 but is rarely been applied in 18 F-labelling [18][19][20] because tracers with high-specific radioactivity are generally desired. 21 Therefore, it was interesting to explore the scope of 18/19 F exchange reactions and its limitations with respect to specific radioactivity.…”

“…4,5 It might also find applications in other fields where there are questions related to response systems, as in plant physiology. There are a number of positronemitting radionuclides like 15 O, 13 N, 11 C, 18 F, 76 Br, and 124 I, as well as metals including 68 Ga and 64 Cu with various properties of interest. Radionuclides like 11 C and halogens, especially 18 F, are of particular interest due to their synthetic potential.…”

“…There are a number of positronemitting radionuclides like 15 O, 13 N, 11 C, 18 F, 76 Br, and 124 I, as well as metals including 68 Ga and 64 Cu with various properties of interest. Radionuclides like 11 C and halogens, especially 18 F, are of particular interest due to their synthetic potential. 6,7 As time is an important parameter in labelling, we were interested in developing a fluorous 8 -labelling strategy, using polyfluorinated compounds as a way to control reactivity, and facilitate the separation of these fluorous precursors from their non-fluorous products, by using fluorous solid-phase extraction 9 as an efficient technology for fast and reliable purification.…”

“…to perform pharmacokinetic studies, making it possible to use F-exchange as a labelling method. We therefore explored [ 18 F]/ 19 F exchange in a series of fluorobenzophenones (1-6), 1-(4-fluorophenyl)ethanone (7), various activated and deactivated fluoro benzenes (8)(9)(10)(11)(12)(13)(14)(15)(16), N-(pentafluorophenyl)benzamide (17), (pentafluorophenyl)formamide (18), (tridecafluorohexyl)benzene (19), tetradecafluorohexane (20), two analogues of WAY-100635 (21)(22), Lapatinib (23), 2,5,6,7,8-pentafluoro-3-methylnaphthoquinone (24) and 1-(2,4-difluorophenyl)-3-(4-fluorophenyl)propan-1-one (25).…”

The 18F‐labelled alkylating agent 2,2,2‐trifluoroethyl triflate: Synthesis and specific activity

“…Direct 18F-19F exchange has been deliberately utilized many times as a means of introducing fluorine-18 into organic molecules (see references in 33) and may, in fact, be the preferred exchange reaction for many aromatic substrates (34). Activated mono-and/or polyhalogenated alkyl groups have also been used as substrates for radiofluorinations.…”