Trifluoromethanesulfonic Acid-Mediated Reaction of 2-Methoxyacetic Acid with Arenes —Clarification of Reaction Behavior and Route for Diarylmethanes and Anthracene Derivatives Formation—

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  • KAMEDA Asami
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • NISHIMORI Hiroki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • OMURA Satohiro
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • KOIKE Masayuki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • HINO Tetsuo
    Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo
  • JOBASHI Takashi
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • MAEYAMA Katsuya
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology
  • YONEZAWA Noriyuki
    Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology

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Other Title
  • トリフルオロメタンスルホン酸存在下での2-メトキシ酢酸と芳香族化合物との反応 —ジアリールメタンおよびアントラセン誘導体生成反応の挙動と経路の解明—
  • Trifluoromethanesulfonic Acid-Mediated Reaction of 2-Methoxyacetic Acid with Arenes. Clarification of Reaction Behavior and Route for Diarylmethanes and Anthracene Derivatives Formation.

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α-Methoxycarboxylic acids 1 undergo decarbonylative α,α-diarylation reaction with arenes 2 in the presence of phosphorus pentoxide-methanesulfonic acid mixture (P2O5–MsOH). However, 2-methoxyacetic acid (1d) shows different reaction behavior from those of other α-carboxylic acids (1). Trifluoromethanesulfonic acid (TfOH)-mediated reaction of 2-methoxyacetic acid (1d) with arenes 2 yields anthracene derivatives 10 in addition to Friedel-Crafts acylation type products and diarylmethanes 4. The reaction behavior was elucidated by estimating the influence of the kind of acidic medium and the substrate structure. Furthermore, based on the results of the reaction of the model compounds for the corresponding suspected reaction pathways, the adequacy of the pathways was evaluated. TfOH-mediated reactions of 2-methoxyacetic acid (1d) with arenes except for that with benzene (2f) proved to proceed via α-hydroxyacetophenone homologues 7 and 11, 1,1-diarylethanediol derivatives 14, and 1,2,2-triarylethanol derivative 17.

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