Communication

CuI-Catalyzed 11C Carboxylation of Boronic Acid Esters: A Rapid and Convenient Entry to 11C-Labeled Carboxylic Acids, Esters, and Amides†

  1. Dr. Patrick J. Riss1,2,*,
  2. Dr. Shuiyu Lu2,
  3. Dr. Sanjay Telu2,
  4. Dr. Franklin I. Aigbirhio1,
  5. Dr. Victor W. Pike2

Article first published online: 3 FEB 2012

DOI: 10.1002/anie.201107263

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 11, pages 2698–2702, March 12, 2012

Additional Information

How to Cite

Riss, P. J., Lu, S., Telu, S., Aigbirhio, F. I. and Pike, V. W. (2012), CuI-Catalyzed 11C Carboxylation of Boronic Acid Esters: A Rapid and Convenient Entry to 11C-Labeled Carboxylic Acids, Esters, and Amides. Angew. Chem. Int. Ed., 51: 2698–2702. doi: 10.1002/anie.201107263

Author Information

  1. 1

    Wolfson Brain Imaging Centre, University of Cambridge, Box 65 Addenbrooke's Hospital, CB2 0QQ, Cambridge (UK)

  2. 2

    Molecular Imaging Branch, National Institute of Mental Health, Bldg 10 Room B3C346A, 10 Center Drive, Bethesda, MD 20892-1003 (USA)

*Wolfson Brain Imaging Centre, University of Cambridge, Box 65 Addenbrooke's Hospital, CB2 0QQ, Cambridge (UK)

  1. †

    P.J.R. was supported by a Medical Research Council (UK) postdoctoral fellowship as a visiting volunteer worker at the NIH. S.T., S.L., and V.W.P. were supported by the Intramural Research Program of the NIH (NIMH). We thank Jinsoo Hong (NIMH) for technical assistance and the NIH Clinical PET department (Chief, Dr. P. Herscovitch) for 11C production.

Publication History

  1. Issue published online: 7 MAR 2012
  2. Article first published online: 3 FEB 2012
  3. Manuscript Revised: 9 JAN 2012
  4. Manuscript Received: 13 OCT 2011

Funded by

  • Medical Research Council
  • NIH

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Keywords:

  • boronic acid esters;
  • carbon-11;
  • carboxylation;
  • positron emission tomography;
  • radiochemistry
Thumbnail image of graphical abstract

Rapid and direct: The carboxylation of boronic acid esters with 11CO2 provides [11C]carboxylic acids as a convenient entry into [11C]esters and [11C]amides (see scheme). This conversion of boronates is tolerant to diverse functional groups (e.g., halo, nitro, or carbonyl).

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