Synlett 2016; 27(01): 25-28
DOI: 10.1055/s-0035-1560592
letter
© Georg Thieme Verlag Stuttgart · New York

Silver-Mediated 18F-Labeling of Aryl-CF3 and Aryl-CHF2 with 18F-Fluoride

Stefan Verhoog
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
,
Lukas Pfeifer
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
,
Tanatorn Khotavivattana
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
,
Samuel Calderwood
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
,
Thomas Lee Collier
Advion BioSystems, 10 Brown Road, Suite 101, Ithaca, NY 14850, USA
,
Katherine Wheelhouse
Medicines Discovery & Development, GlaxoSmithKline, R&D, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK
,
Matthew Tredwell
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
,
Véronique Gouverneur*
University of Oxford, Chemistry Research laboratory, 12 Mansfield Road, OX1 3TA, Oxford, UK   Email: veronique.gouverneur@chem.ox.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 16 October 2015

Accepted after revision: 03 November 2015

Publication Date:
20 November 2015 (eFirst)

In celebration of Prof. Steven Ley’s 70th birthday

Abstract

We report the synthesis of [18F]arylCF3 and [18F]arylCHF2 derivatives from arylCF2Br and arylCHFCl precursors applying a silver-mediated halogen exchange with [18F]fluoride. In the absence of Ag(I)OTf, no reaction takes place at room temperature for both classes of substrates; this result demonstrates the beneficial role of silver(I) as a means to induce 18F-incorporation under very mild conditions.

Supporting Information

 
  • References and Notes

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