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Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes

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    Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes
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    • Katarina J. Makaravage
      Katarina J. Makaravage
      Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
      More by Katarina J. Makaravage
    • Xia Shao
      Xia Shao
      Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States
      More by Xia Shao
    • Allen F. Brooks
      Allen F. Brooks
      Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States
      More by Allen F. Brooks
      Orcidhttp://orcid.org/0000-0003-3773-3024
    • Lingyun Yang
      Lingyun Yang
      Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States
      Center of Drug Discovery, State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, P.R. China
      More by Lingyun Yang
    • Melanie S. Sanford*
      Melanie S. Sanford
      Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
      *E-mail: [email protected]
      More by Melanie S. Sanford
      Orcidhttp://orcid.org/0000-0001-9342-9436
    • Peter J. H. Scott*
      Peter J. H. Scott
      Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States
      *E-mail: [email protected]
      More by Peter J. H. Scott
      Orcidhttp://orcid.org/0000-0002-6505-0450
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 6, 1530–1533
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    https://doi.org/10.1021/acs.orglett.8b00242
    Published February 27, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses commercially available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected radiochemical yield (RCY).

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.8b00242.

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    40. Thomas C. Wilson, Thomas Cailly, Véronique Gouverneur. Boron reagents for divergent radiochemistry. Chemical Society Reviews 2018, 47 (18) , 6990-7005. https://doi.org/10.1039/C8CS00499D
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 6, 1530–1533
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.8b00242
    Published February 27, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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