Iron-catalyzed stereospecific activation of olefinic C-H bonds with grignard reagent for synthesis of substituted olefins

Laurean Ilies, Sobi Asako, Eiichi Nakamura

    Research output: Contribution to journalArticlepeer-review

    136 Citations (Scopus)

    Abstract

    The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several lines of evidence suggest that the reaction proceeds via iron-catalyzed olefinic C-H bond activation rather than an oxidative Mizoroki-Heck-type reaction.

    Original languageEnglish
    Pages (from-to)7672-7675
    Number of pages4
    JournalJournal of the American Chemical Society
    Volume133
    Issue number20
    DOIs
    Publication statusPublished - May 25 2011

    ASJC Scopus subject areas

    • Catalysis
    • General Chemistry
    • Biochemistry
    • Colloid and Surface Chemistry

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