Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction

Yuma Komata, Masashi Yoshikawa, Yasuhiro Tamura, Hiroaki Wada, Atsushi Shimojima, Kazuyuki Kuroda

    Research output: Contribution to journal › Article

    1 Citation (Scopus)

    Abstract

    Alkoxychlorosilanes are scientifically and industrially important toward preparing silicone and silica as well as preparation of siloxane-based nanomaterials by stepwise reactions of Si-OR (R=alkyl) and Si-Cl groups. Intermolecular exchange of alkoxy and chloro groups between alkoxysilanes and chlorosilanes (functional group exchange reaction) provides an efficient and environmentally benign route to alkoxychlorosilanes. BiCl3 as a Lewis acid catalyst can promote the functional group exchange reactions more efficiently than conventional acid catalysts. Higher reactivity has been observed for chlorosilanes with smaller numbers of Si-CH3 groups and for alkoxysilanes with larger numbers of Si-CH3 groups. The reaction mechanism is proposed and selective syntheses of alkoxychlorosilanes are demonstrated. These findings also enable us to synthesize an organotrialkoxysilane with four different substituents.

    Original languageEnglish
    JournalChemistry - An Asian Journal
    DOIs
    Publication statusAccepted/In press - 2016

    Fingerprint

    Siloxanes
    Lewis Acids
    Nanostructures
    Silicones
    Silicon Dioxide
    Functional groups
    Catalysts
    Acids
    Nanostructured materials
    alkoxyl radical

    Keywords

    • Alkoxysilane
    • Chlorosilane
    • Exchange reaction
    • Lewis acid
    • Selective synthesis

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction. / Komata, Yuma; Yoshikawa, Masashi; Tamura, Yasuhiro; Wada, Hiroaki; Shimojima, Atsushi; Kuroda, Kazuyuki.

    In: Chemistry - An Asian Journal, 2016.

    Research output: Contribution to journal › Article

    Komata, Y, Yoshikawa, M, Tamura, Y, Wada, H, Shimojima, A & Kuroda, K 2016, 'Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction', Chemistry - An Asian Journal. https://doi.org/10.1002/asia.201601120
    Komata Y, Yoshikawa M, Tamura Y, Wada H, Shimojima A, Kuroda K. Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction. Chemistry - An Asian Journal. 2016. https://doi.org/10.1002/asia.201601120
    Komata, Yuma ; Yoshikawa, Masashi ; Tamura, Yasuhiro ; Wada, Hiroaki ; Shimojima, Atsushi ; Kuroda, Kazuyuki. / Selective Formation of Alkoxychlorosilanes and Organotrialkoxysilane with Four Different Substituents by Intermolecular Exchange Reaction. In: Chemistry - An Asian Journal. 2016.
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    abstract = "Alkoxychlorosilanes are scientifically and industrially important toward preparing silicone and silica as well as preparation of siloxane-based nanomaterials by stepwise reactions of Si-OR (R=alkyl) and Si-Cl groups. Intermolecular exchange of alkoxy and chloro groups between alkoxysilanes and chlorosilanes (functional group exchange reaction) provides an efficient and environmentally benign route to alkoxychlorosilanes. BiCl3 as a Lewis acid catalyst can promote the functional group exchange reactions more efficiently than conventional acid catalysts. Higher reactivity has been observed for chlorosilanes with smaller numbers of Si-CH3 groups and for alkoxysilanes with larger numbers of Si-CH3 groups. The reaction mechanism is proposed and selective syntheses of alkoxychlorosilanes are demonstrated. These findings also enable us to synthesize an organotrialkoxysilane with four different substituents.",
    keywords = "Alkoxysilane, Chlorosilane, Exchange reaction, Lewis acid, Selective synthesis",
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    AU - Komata, Yuma

    AU - Yoshikawa, Masashi

    AU - Tamura, Yasuhiro

    AU - Wada, Hiroaki

    AU - Shimojima, Atsushi

    AU - Kuroda, Kazuyuki

    PY - 2016

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    N2 - Alkoxychlorosilanes are scientifically and industrially important toward preparing silicone and silica as well as preparation of siloxane-based nanomaterials by stepwise reactions of Si-OR (R=alkyl) and Si-Cl groups. Intermolecular exchange of alkoxy and chloro groups between alkoxysilanes and chlorosilanes (functional group exchange reaction) provides an efficient and environmentally benign route to alkoxychlorosilanes. BiCl3 as a Lewis acid catalyst can promote the functional group exchange reactions more efficiently than conventional acid catalysts. Higher reactivity has been observed for chlorosilanes with smaller numbers of Si-CH3 groups and for alkoxysilanes with larger numbers of Si-CH3 groups. The reaction mechanism is proposed and selective syntheses of alkoxychlorosilanes are demonstrated. These findings also enable us to synthesize an organotrialkoxysilane with four different substituents.

    AB - Alkoxychlorosilanes are scientifically and industrially important toward preparing silicone and silica as well as preparation of siloxane-based nanomaterials by stepwise reactions of Si-OR (R=alkyl) and Si-Cl groups. Intermolecular exchange of alkoxy and chloro groups between alkoxysilanes and chlorosilanes (functional group exchange reaction) provides an efficient and environmentally benign route to alkoxychlorosilanes. BiCl3 as a Lewis acid catalyst can promote the functional group exchange reactions more efficiently than conventional acid catalysts. Higher reactivity has been observed for chlorosilanes with smaller numbers of Si-CH3 groups and for alkoxysilanes with larger numbers of Si-CH3 groups. The reaction mechanism is proposed and selective syntheses of alkoxychlorosilanes are demonstrated. These findings also enable us to synthesize an organotrialkoxysilane with four different substituents.

    KW - Alkoxysilane

    KW - Chlorosilane

    KW - Exchange reaction

    KW - Lewis acid

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