Nucleophilic ortho allylation of aryl and heteroaryl sulfoxides

Andrew J. Eberhart, Jason E. Imbriglio, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Aryl and heteroaryl sulfoxides undergo ortho allylation upon treatment with Tf 2O and allylsilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods including Kumada-Corriu cross-coupling of the organosulfanyl group. © 2011 American Chemical Society.
    Original languageEnglish
    Pages (from-to)5882-5885
    Number of pages3
    JournalOrganic Letters
    Volume13
    Issue number21
    DOIs
    Publication statusPublished - 4 Nov 2011

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