Synthesis of 4-[18F]fluorophenyl-alkenes and -arenes via palladium-catalyzed coupling of 4-[18F]fluoroiodobenzene with vinyl and aryl tin reagents

Abstract

The cross-coupling reaction of 4-[18F]fluoroiodobenzene 3a with vinyl or aryl tin reagents in the presence of tetrakis(triphenylphosphine)palladium was found to provide a convenient and rapid method for the preparation of 4-[18F]fluorostyrene or 4-[18F]fluorobiphenyl within 45-50 min and 47% or 86% radiochemical yields, respectively, counted from 3a. (E)-N-{3-(4-[18F]fluorophenyl}prop-2-enyl]piperidine 2a was obtained within 45 min and in 80% radiochemical yield from 3a. 4-[18F]Fluorobromobenzene 4a was prepared in 24-48% yield from 2-nitro-5-bromobenzaldehyde and [18F]KF in 95 min. © Acta Chemica Scandinavica 1998.