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Palladium-Catalyzed C(sp3)—H Oxygenation via Electrochemical Oxidation

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    Palladium-Catalyzed C(sp3)—H Oxygenation via Electrochemical Oxidation
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    † State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
    ‡ Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No. 130, Shanghai 200237, China
    *[email protected]
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    Cite this: J. Am. Chem. Soc. 2017, 139, 8, 3293–3298
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    https://doi.org/10.1021/jacs.7b01232
    Published February 8, 2017
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    Abstract

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    Palladium-catalyzed C—H activation/C—O bond-forming reactions have emerged as attractive tools for organic synthesis. Typically, these reactions require strong chemical oxidants, which convert organopalladium(II) intermediates into the PdIII or PdIV oxidation state to promote otherwise challenging C—O reductive elimination. However, previously reported oxidants possess significant disadvantages, including poor atom economy, high cost, and the formation of undesired byproducts. To overcome these issues, we report an electrochemical strategy that takes advantage of anodic oxidation of PdII to induce selective C—O reductive elimination with a variety of oxyanion coupling partners.

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    Cite this: J. Am. Chem. Soc. 2017, 139, 8, 3293–3298
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