Communication

Palladium-Catalyzed Allylic Fluorination†

  1. Charlotte Hollingworth1,
  2. Dr. Amaruka Hazari1,
  3. Matthew N. Hopkinson1,
  4. Dr. Matthew Tredwell1,
  5. Elena Benedetto1,
  6. Dr. Mickael Huiban2,
  7. Prof. Antony D. Gee3,
  8. Dr. John M. Brown1,*,
  9. Prof. Véronique Gouverneur1,*

Article first published online: 8 FEB 2011

DOI: 10.1002/anie.201007307

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 50, Issue 11, pages 2613–2617, March 7, 2011

Additional Information

How to Cite

Hollingworth, C., Hazari, A., Hopkinson, M. N., Tredwell, M., Benedetto, E., Huiban, M., Gee, A. D., Brown, J. M. and Gouverneur, V. (2011), Palladium-Catalyzed Allylic Fluorination. Angew. Chem. Int. Ed., 50: 2613–2617. doi: 10.1002/anie.201007307

Author Information

  1. 1

    Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865-275-644

  2. 2

    GSK Clinical Imaging Centre, Hammersmith Hospital, London W12 0NN (UK)

  3. 3

    Division of Imaging Sciences and Bioengineering, King's College London, London, SE1 7EH (UK)

*Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865-275-644

  1. †

    We thank Dr. S. Fletcher for very helpful discussions. This research was financially supported by the EPSRC (C.H., A.H., M.T.), GSK (M.H.), the CRUK (M.T.), the European Union FP7-ITN-238434 (E.B.), and the Leverhulme Trust (J.M.B.).

Publication History

  1. Issue published online: 2 MAR 2011
  2. Article first published online: 8 FEB 2011
  3. Manuscript Received: 20 NOV 2010

Funded by

  • EPSRC
  • GSK
  • CRUK
  • European Union. Grant Number: FP7-ITN-238434
  • Leverhulme Trust

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Keywords:

  • allylic fluorination;
  • fluorides;
  • homogeneous catalysis;
  • palladium;
  • positron emission tomography
Thumbnail image of graphical abstract

Mild and rapid: The title reaction is presented and its applicability to 18F radiolabeling is demonstrated (see scheme; TBAF=tetra-n-butylammonium fluoride, THF=tetrahydrofuran, dba=dibenzylideneacetone). The use of p-nitrobenzoate as the leaving group is significant to the success of this catalytic organometallic fluorination process. A range of allylic fluorides were synthesized by this method.

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