Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide

Keita Hyodo, Hikaru Nonobe, Shuhei Nishinaga, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    29 Citations (Scopus)

    Abstract

    Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.

    Original languageEnglish
    Pages (from-to)4002-4005
    Number of pages4
    JournalTetrahedron Letters
    Volume55
    Issue number29
    DOIs
    Publication statusPublished - Jul 16 2014

    Keywords

    • Boron
    • Negishi coupling
    • Phenacenes
    • Suzuki-Miyaura coupling
    • Zinc

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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