Synthesis of macrocyclic heteroarylenes by consecutive inter- and intramolecular cycloadditions of thiophenylene-tethered triynes

Takanori Shibata, Masako Fujimoto, Takashi Otani

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    Abstract

    Consecutive inter- and intramolecular [2+2+2] cycloadditions of various thiophenylene-tethered triynes were comprehensively studied by using chiral Rh catalysts. When we started from 2,3- and 3,4-thiophenylene-tethered substrates, dimerization proceeded and chiral tetraheteroarylenes were obtained. In contrast, reactions of 2,5-thiophenylene-tethered substrates gave hexaheteroarylenes as trimers. When bis- and tris(2,5-thiophenylene)-tethered triynes were used, mixtures of dimers and trimers were obtained, which included macrocyclic systems that contained up to 12 aromatic rings, and their photophysical properties were measured.

    Original languageEnglish
    Pages (from-to)8453-8461
    Number of pages9
    JournalTetrahedron
    Volume70
    Issue number45
    DOIs
    Publication statusPublished - 2014 Nov 11

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    Keywords

    • Asymmetric synthesis
    • Chirality
    • Cycloaddition
    • Heteroarylenes
    • Macrocycles
    • Rhodium
    • Thiophene

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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