Fast and High-Yield Microreactor Syntheses of ortho-Substituted [18F]Fluoroarenes from Reactions of [18F]Fluoride Ion with Diaryliodonium Salts
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Abstract
A microreactor was applied to produce ortho-substituted [(18)F]fluoroarenes from the reactions of cyclotron-produced [(18)F]fluoride ion (t(1/2) = 109.7 min) with diaryliodonium salts. The microreactor provided a very convenient means for running sequential reactions rapidly with small amounts of reagents under well-controlled conditions, thereby allowing reaction kinetics to be followed and Arrhenius activation energies (E(a)) to be measured. Prepared symmetrical iodonium chlorides (Ar(2)I(+)Cl(-)) rapidly ( 2,4,6-tri-Me > Br > Me > Et approximately (i)Pr >> H > OMe. For (2-methyphenyl)(phenyl)iodonium chloride, the time-course of reaction product selectivity was constant and consistent with the operation of the Curtin-Hammett principle. These results will aid in the design of diaryliodonium salt precursors to (18)F-labeled tracers for molecular imaging.
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