Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

Sean Preshlock; Samuel Calderwood; Stefan Verhoog; Matthew Tredwell; Mickael Huiban; Antje Hienzsch; Stefan Gruber; Thomas C. Wilson; Nicholas J. Taylor; Thomas Cailly; Michael Schedler; Thomas Lee Collier; Jan Passchier; René Smits; Jan Mollitor; Alexander Hoepping; Marco Mueller; Christophe Genicot; Joël Mercier; Véronique Gouverneur

doi:10.1039/C6CC03295H

Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications†

Sean Preshlock,^a Samuel Calderwood,‡^a Stefan Verhoog,‡^a Matthew Tredwell,^a Mickael Huiban,^b Antje Hienzsch,^c Stefan Gruber,^a Thomas C. Wilson,^a Nicholas J. Taylor,^a Thomas Cailly,^ad Michael Schedler,^a Thomas Lee Collier,^e Jan Passchier,^b René Smits,^c Jan Mollitor,^c Alexander Hoepping,^c Marco Mueller,^c Christophe Genicot,^f Joël Mercier^f and Véronique Gouverneur*^a

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* Corresponding authors

^a University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, OX1 3TA Oxford, UK
E-mail: veronique.gouverneur@chem.ox.ac.uk

^b Imanova, Burlington Danes building Imperial College, London Hammersmith Hospital, Du Cane Road, London W12 0NN, UK

^c ABX GmbH Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany

^d Normandie University, UNICAEN, CERMN, F-14032 Caen, France

^e Advion BioSystems, 10 Brown Road, Suite 101, Ithaca, NY 14850, USA

^f Global Chemistry, UCB New Medicines, UCB Biopharma sprl, 1420 Braine-L'Alleud, Belgium

Abstract

[¹⁸F]FMTEB, [¹⁸F]FPEB, [¹⁸F]flumazenil, [¹⁸F]DAA1106, [¹⁸F]MFBG, [¹⁸F]FDOPA, [¹⁸F]FMT and [¹⁸F]FDA are prepared from the corresponding arylboronic esters and [¹⁸F]KF/K₂₂₂ in the presence of Cu(OTf)₂py₄. The method was successfully applied using three radiosynthetic platforms, and up to 26 GBq of non-carrier added starting activity of ¹⁸F-fluoride.

This article is part of the themed collection: Celebrating our 2019 Prize and Award winners

Chemical Communications

Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications†

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Enhanced copper-mediated ¹⁸F-fluorination of aryl boronic esters provides eight radiotracers for PET applications

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