Aromatic homolytic substitution using solid phase synthesis

Steven M. Allin, W. Russell Bowman, Rehana Karim, Shahzad S. Rahman

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.

    Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors.
    Original languageEnglish
    Pages (from-to)4306-4316
    JournalTetrahedron Letters
    Volume62
    Issue number18
    DOIs
    Publication statusPublished - 1 May 2006

    Keywords

    • Aryl radicals
    • Radical cyclisation
    • solid-phase synthesis
    • Microwave
    • Benzoimidazoles

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