Synthesis of Octaaryl Naphthalenes and Anthracenes with Different Substituents

Shin Suzuki, Kenichiro Itami, Junichiro Yamaguchi

    Research output: Contribution to journalArticle

    11 Citations (Scopus)

    Abstract

    A synthesis of multiply arylated naphthalenes and anthracenes with eight different substituents has been accomplished. The key intermediates are tetraarylthiophene S-oxides, which are synthesized through a method involving sequential C−H arylation and cross-coupling from 3-methoxythiophene, followed by oxidation of the sulfur atom. The resulting tetraarylthiophene S-oxides can be converted into a tetraaryl benzynes or naphthalynes and then merged through [4+2] cycloaddition reaction with another tetraarylthiophene S-oxide, thereby resulting in the programmed synthesis of octaarylnaphthalenes and octaarylanthracenes.

    Original languageEnglish
    Pages (from-to)15010-15013
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume56
    Issue number47
    DOIs
    Publication statusPublished - 2017 Nov 20

    Fingerprint

    Anthracenes
    Naphthalenes
    Anthracene
    Naphthalene
    Oxides
    Cycloaddition
    Sulfur
    Atoms
    Oxidation

    Keywords

    • arenes
    • arynes
    • cycloaddition
    • molecular diversity
    • polycycles

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

    Cite this

    Synthesis of Octaaryl Naphthalenes and Anthracenes with Different Substituents. / Suzuki, Shin; Itami, Kenichiro; Yamaguchi, Junichiro.

    In: Angewandte Chemie - International Edition, Vol. 56, No. 47, 20.11.2017, p. 15010-15013.

    Research output: Contribution to journalArticle

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