Synthesis of m -terphenyl derivatives via domino Diels-Alder/Retro-Diels- Alder reaction of 1,3-dienic δ-sultones with alkynes

Jens Gaitzsch, Victor Rogachev, Martin Zahel, Peter Metz

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    Abstract

    A highly regioselective synthetic method based on the domino Diels-Alder/retro-Diels-Alder reaction (DA/RDA) of 1,3-dienic δ-sultones with alkynes provides substituted m-terphenyls by elimination of SO3. A variety of δ-sultones and alkynes were examined to determine the scope of the reaction. The de novo synthesized aromatic products were obtained using thermal, microwave, and high-pressure activation.

    Original languageEnglish
    Article numberSS-2013-Z0580-OP
    Pages (from-to)531-536
    Number of pages6
    JournalSynthesis (Germany)
    Volume46
    Issue number4
    DOIs
    Publication statusPublished - Feb 2014

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    Keywords

    • alkynes
    • Diels-Alder reaction
    • high pressure
    • m -terphenyls
    • sultones

    ASJC Scopus subject areas

    • Organic Chemistry
    • Catalysis

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