Communication

Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride†

  1. Dr. Zhanghua Gao1,
  2. Dr. Yee Hwee Lim1,
  3. Dr. Matthew Tredwell1,
  4. Dr. Lei Li1,
  5. Stefan Verhoog1,
  6. Dr. Matthew Hopkinson1,
  7. Wojciech Kaluza1,
  8. Dr. Thomas Lee Collier3,
  9. Dr. Jan Passchier2,
  10. Dr. Mickael Huiban2,
  11. Prof. Véronique Gouverneur1,*

Article first published online: 25 MAY 2012

DOI: 10.1002/anie.201201502

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 27, pages 6733–6737, July 2, 2012

Additional Information

How to Cite

Gao, Z., Lim, Y. H., Tredwell, M., Li, L., Verhoog, S., Hopkinson, M., Kaluza, W., Collier, T. L., Passchier, J., Huiban, M. and Gouverneur, V. (2012), Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride. Angew. Chem. Int. Ed., 51: 6733–6737. doi: 10.1002/anie.201201502

Author Information

  1. 1

    Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK)

  2. 2

    Imanova Ltd Burlington Danes Building Imperial College London Hammersmith Hospital, Du Cane Road, London W12 0NN (UK)

  3. 3

    Advion BioSystems, Inc. 10 Brown Road, Ithaca, NY 14850 (USA)

*Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK)

  1. †

    The authors thank the EPSRC (to Z.G., M.T., M.H.), the CRUK (to Z.G., M.T.), GSK (to M.H.), the A*STAR NSS Overseas Ph.D. Scholarship (to Y.H.L.), the K. C. Wong Education Foundation (to L.L.), and Advion BioSystems for generous funding, Dr. John M. Brown FRS for discussions and Dr. Oscar Lozano for technical assistance.

Publication History

  1. Issue published online: 27 JUN 2012
  2. Article first published online: 25 MAY 2012
  3. Manuscript Revised: 5 APR 2012
  4. Manuscript Received: 23 FEB 2012

Funded by

  • EPSRC
  • CRUK
  • GSK
  • K. C. Wong Education Foundation

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (414K)

Keywords:

  • fluoride ions;
  • fluorination;
  • oxidation;
  • phenol umpolung;
  • radiochemistry
Thumbnail image of graphical abstract

The radiochemical synthesis of [18F]4-fluorophenols is based on phenol umpolung under oxidative conditions and direct nucleophilic fluorination with [18F]fluoride (see scheme, TBAF=tetra-n-butylammonium fluoride, TFA=trifluoroacetic acid). Readily available O-unprotected 4-tert-butyl phenols are used as precursors in this one-pot protocol. The reaction is completed in less than 30 minutes at room temperature and can be performed using standard or microfluidic technology.

View Full Article with Supporting Information (HTML) Get PDF (414K)