Emerging organosulfonium electrophiles as unique reagents for carbonsulfur bond formation: Prospects in synthetic chemistry of organosulfur compounds

Fuyuki Aida, Kenichi Oyaizu

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    Carbon-sulfur (C-S) bond formation is one of the important synthetic routes in organic chemistry. Among sulfur sources for C-S bond formation, organosulfur cations (RS+) and their synthetic equivalents are unique reagents. These cationic sulfur species are easily prepared as compared with the oxonium analogues, because of their low ionization potentials. This review describes various synthetic methods for C-S bond formation, mainly focusing on electrophilic reactions, addition to olefins, and substitution to aromatic rings. A breakthrough has been anticipated for RS+ electrophiles, based on their versatile utility in aromatic polymer synthesis.

    Original languageEnglish
    Pages (from-to)102-109
    Number of pages8
    JournalChemistry Letters
    Volume45
    Issue number2
    DOIs
    Publication statusPublished - 2016

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    Sulfur
    Carbon
    Aromatic polymers
    Addition reactions
    Ionization potential
    Alkenes
    Cations
    Substitution reactions

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

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    abstract = "Carbon-sulfur (C-S) bond formation is one of the important synthetic routes in organic chemistry. Among sulfur sources for C-S bond formation, organosulfur cations (RS+) and their synthetic equivalents are unique reagents. These cationic sulfur species are easily prepared as compared with the oxonium analogues, because of their low ionization potentials. This review describes various synthetic methods for C-S bond formation, mainly focusing on electrophilic reactions, addition to olefins, and substitution to aromatic rings. A breakthrough has been anticipated for RS+ electrophiles, based on their versatile utility in aromatic polymer synthesis.",
    author = "Fuyuki Aida and Kenichi Oyaizu",
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    AU - Oyaizu, Kenichi

    PY - 2016

    Y1 - 2016

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    AB - Carbon-sulfur (C-S) bond formation is one of the important synthetic routes in organic chemistry. Among sulfur sources for C-S bond formation, organosulfur cations (RS+) and their synthetic equivalents are unique reagents. These cationic sulfur species are easily prepared as compared with the oxonium analogues, because of their low ionization potentials. This review describes various synthetic methods for C-S bond formation, mainly focusing on electrophilic reactions, addition to olefins, and substitution to aromatic rings. A breakthrough has been anticipated for RS+ electrophiles, based on their versatile utility in aromatic polymer synthesis.

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