Direct thiolation and seienation of aryl C-H bonds catalyzed by palladium or nickel

Masayuki Iwasaki, Yasushi Nishihara

    Research output: Contribution to journalReview articlepeer-review

    1 Citation (Scopus)

    Abstract

    Over the last two decades, transition-metal-catalyzed chelate-assisted direct functionalization of aryl C-H bonds has been well developed. These methodologies realized the efficient carbon -carbon, carbon-oxygen, carbon-nitrogen, and carbon-halogen bond formations. However, the related catalytic direct thiolation and selenation have yet to be disclosed despite the utilities of organosulfur and organoselenium compounds as building blocks in bioactive molecules and functional organic materials. Very recently, several research groups including our group have developed chelate-assisted intermolecular direct thiolation and selenation by using various transition metal catalysts, such as palladium, rhodium, nickel, copper, ruthenium, and cobalt. This article describes our recent studies on chelate-assisted catalytic direct thiolation and selenation of aryl C-H bonds. The reactions with thiols, disulfides, selenols, diselenides, and elemental selenium proceeded well in the presence of palladium or nickel catalyst to provide a variety of organochalcogen compounds. In addition, an appropriate choice of the directing group can be made to control the reaction sites.

    Original languageEnglish
    Pages (from-to)11-20
    Number of pages10
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume76
    Issue number1
    DOIs
    Publication statusPublished - 2018

    Keywords

    • Benzoisoselenazolones
    • Directing groups
    • Diselenides
    • Disulfides
    • Elemental selenium
    • Nickel
    • Palladium
    • Selenation
    • Site-selective functionalization
    • Thiolation

    ASJC Scopus subject areas

    • Organic Chemistry

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