N-Heterocyclic Carbene-catalyzed Difluorocarbene Generation and its Application to Aryl Difluoromethyl Ether Synthesis

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  • Fuchibe Kohei
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Koseki Yuta
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Sasagawa Hisashi
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Ichikawa Junji
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba

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Other Title
  • <i>N</i>-Heterocyclic Carbene-catalyzed Difluorocarbene Generation and its Application to Aryl Difluoromethyl Ether Synthesis

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Abstract

NHC-catalyzed generation of difluorocarbene from trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA) enables the synthesis of enol difluoromethyl ethers starting from cyclohexenones and tetralones. The resultant enol difluoromethyl ethers were successively dehydrogenated with DDQ to furnish aryl difluoromethyl ethers in good to high yield.

Journal

  • Chemistry Letters

    Chemistry Letters 40 (10), 1189-1191, 2011

    The Chemical Society of Japan

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