Facile synthesis of cyclic polyphenylenes by consecutive inter- and intramolecular cycloadditions of ortho -, meta -, and para -phenylene-tethered triynes

Takanori Shibata, Masako Fujimoto, Hiroyuki Hirashima, Tatsuya Chiba, Kohei Endo

    Research output: Contribution to journalArticle

    20 Citations (Scopus)

    Abstract

    Consecutive inter- and intramolecular [2+2+2] cycloadditions of various phenylene-tethered triynes were comprehensively studied by using chiral rhodium catalysts. ortho-Phenylene-tethered triynes gave chiral o,o,o,o-tetraphenylenes in high-to-excellent enantiomeric excess as dimers. meta-Phenylene-tethered triynes gave chiral o,m,o,m-tetraphenylenes in moderate enantiomeric excess as dimers along with hexaphenylenes as trimers. This is the first synthesis of cis-o,m,o,m-tetraphenylenes; one structure was ascertained by X-ray crystal structure analysis. para-Phenylene-tethered triynes gave o,p,o,p,o,p- hexaphenylenes as trimers along with the formation of o,p,o,p,o,p,o,p- octaphenylenes as tetramers. 1 Introduction 2 Results and Discussion 2.1 ortho-Phenylene-Tethered Triynes 2.2 Naphthylene-Tethered Triynes 2.3 meta-Phenylene-Tethered Triynes 2.4 para-Phenylene-Tethered Triynes 3 Conclusion.

    Original languageEnglish
    Article numberSS-2012-Z0614-FA
    Pages (from-to)3269-3284
    Number of pages16
    JournalSynthesis (Germany)
    Volume44
    Issue number21
    DOIs
    Publication statusPublished - 2012

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    Cycloaddition
    Dimers
    Rhodium
    Crystal structure
    X rays
    Catalysts

    Keywords

    • asymmetric synthesis
    • axial chirality
    • chiral catalysts
    • cycloaddition
    • polyphenylenes
    • rhodium

    ASJC Scopus subject areas

    • Organic Chemistry
    • Catalysis

    Cite this

    Facile synthesis of cyclic polyphenylenes by consecutive inter- and intramolecular cycloadditions of ortho -, meta -, and para -phenylene-tethered triynes. / Shibata, Takanori; Fujimoto, Masako; Hirashima, Hiroyuki; Chiba, Tatsuya; Endo, Kohei.

    In: Synthesis (Germany), Vol. 44, No. 21, SS-2012-Z0614-FA, 2012, p. 3269-3284.

    Research output: Contribution to journalArticle

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