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Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids

Authors

  • Joe C. T. Leung,

    1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
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    • These authors contributed equally to this work.

  • Claire Chatalova-Sazepin,

    1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
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    • These authors contributed equally to this work.

  • Julian G. West,

    1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
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  • Montserrat Rueda-Becerril,

    1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
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  • Prof. Jean-François Paquin,

    1. Canada Research Chair in Organic and Medicinal Chemistry, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V0A6 (Canada)
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  • Prof. Glenn M. Sammis

    Corresponding author
    1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
    • Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada)
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  • This work was supported by the University of British Columbia (UBC), the Université Laval, NSERC, the Canadian Research Chair program, a doctoral fellowship from the Consejo Nacional de Ciencia y Tecnología (CONACyT) to M.R.-B., a doctoral fellowship from UBC to C.C.S., and a doctoral fellowship NSERC to J.C.T.L.

Abstract

original image

Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron-poor 2-aryloxy and 2-aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single-electron transfer.

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