Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions

Sobi Asako, Jakob Norinder, Laurean Ilies, Naohiko Yoshikai, Eiichi Nakamura

    Research output: Contribution to journalArticlepeer-review

    53 Citations (Scopus)

    Abstract

    An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C-H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.

    Original languageEnglish
    Pages (from-to)1481-1485
    Number of pages5
    JournalAdvanced Synthesis and Catalysis
    Volume356
    Issue number7
    DOIs
    Publication statusPublished - May 5 2014

    Keywords

    • C-H activation
    • allylation
    • arenes
    • iron
    • pyrazoles

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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