Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

Toshimasa Okita, Masaaki Komatsuda, Ami N. Saito, Tomoya Hisada, Tomoaki T. Takahara, Keito P. Nakayama, Ryota Isshiki, Ryosuke Takise, Kei Muto, Junichiro Yamaguchi

    Research output: Contribution to journalArticle

    4 Citations (Scopus)

    Abstract

    A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a SNAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.

    Original languageEnglish
    Pages (from-to)1358-1361
    Number of pages4
    JournalAsian Journal of Organic Chemistry
    Volume7
    Issue number7
    DOIs
    Publication statusPublished - 2018 Jul 1

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    Esters
    Bearings (structural)
    Ethers
    Palladium
    Functional groups
    Ligands
    Catalysts
    Electrons
    dibenzofuran

    Keywords

    • C−H activation
    • decarbonylation
    • dibenzofurans
    • ethers
    • palladium

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Dibenzofuran Synthesis : Decarbonylative Intramolecular C−H Arylation of Aromatic Esters. / Okita, Toshimasa; Komatsuda, Masaaki; Saito, Ami N.; Hisada, Tomoya; Takahara, Tomoaki T.; Nakayama, Keito P.; Isshiki, Ryota; Takise, Ryosuke; Muto, Kei; Yamaguchi, Junichiro.

    In: Asian Journal of Organic Chemistry, Vol. 7, No. 7, 01.07.2018, p. 1358-1361.

    Research output: Contribution to journalArticle

    Okita, T, Komatsuda, M, Saito, AN, Hisada, T, Takahara, TT, Nakayama, KP, Isshiki, R, Takise, R, Muto, K & Yamaguchi, J 2018, 'Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters', Asian Journal of Organic Chemistry, vol. 7, no. 7, pp. 1358-1361. https://doi.org/10.1002/ajoc.201800207
    Okita, Toshimasa ; Komatsuda, Masaaki ; Saito, Ami N. ; Hisada, Tomoya ; Takahara, Tomoaki T. ; Nakayama, Keito P. ; Isshiki, Ryota ; Takise, Ryosuke ; Muto, Kei ; Yamaguchi, Junichiro. / Dibenzofuran Synthesis : Decarbonylative Intramolecular C−H Arylation of Aromatic Esters. In: Asian Journal of Organic Chemistry. 2018 ; Vol. 7, No. 7. pp. 1358-1361.
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    AU - Hisada, Tomoya

    AU - Takahara, Tomoaki T.

    AU - Nakayama, Keito P.

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