Synthesis of Novel Trifluoromethyl-bearing Bifunctional Acyl-acceptant Arenes: 2,2'-Bis(trifluoromethylated aryloxy)biphenyls

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  • Okamoto Akiko
    Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • Maeyama Katsuya
    Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • Noguchi Keiichi
    Instrumentation Analysis Center, Tokyo University of Agriculture and Technology
  • Oike Hideaki
    Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • Murakami Yoshihiko
    Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • Yonezawa Noriyuki
    Department of Organic & Polymer Materials Chemistry, Tokyo University of Agriculture and Technology

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Novel bifunctional acyl-acceptant biphenyls bearing trifluoromethylated aroyloxy groups were successfully synthesized in high yields via TfOH-mediated electrophilic aromatic aroylation of fluorobenzene with CF3-bearing aroyl chlorides followed by nucleophilic aromatic substitution with 2,2’-biphenol. Similarly, 2,2’-bis(trifluoromethylphenoxy)biphenyl was synthesized via nucleophilic aromatic substitution of 4-fluorobenzotrifluoride with 2,2’-biphenol. These 2,2’-bis(trifluoromethylated aryloxy)biphenyls show good regioselectivity and successive reactivity in electrophilic aromatic aroylation with p-toluic acid/p-toluoyl chloride according to the structure of the substrate biphenyls, implying their sufficient potential as acyl-accepting precursor molecules for synthesis of aromatic compounds bearing characteristic interfacial properties attributed to CF3 groups.<br>

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