Regioselective C–H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins

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  • Xu Lu
    Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan
  • Ryohei Kawazu
    Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan
  • Jizhou Song
    Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan
  • Yusuke Yoshigoe
    Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan
  • Takeru Torigoe
    Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan
  • Yoichiro Kuninobu
    Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan

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説明

<jats:p>A regioselective radical C–H trifluoromethylation of aromatic compounds was developed using cyclodextrins (CDs) as additives. The C–H trifluoromethylation proceeded with high regioselectivity to afford the product in good yield, even on the gram scale. In the presence of CDs, some substrates underwent a single trifluoromethylation selectively, whereas mixtures of single- and double-trifluoromethylated products were formed in the absence of the CD. <jats:sup>1</jats:sup>H NMR experiments indicated that the regioselectivity was controlled by the inclusion of a substrate inside the CD cavity.</jats:p>

収録刊行物

  • Organic Letters

    Organic Letters 23 (11), 4327-4331, 2021-05-14

    American Chemical Society (ACS)

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