N-methyl-benzothiazolium salts as carbon Lewis acids for Si-H σ bond activation and catalytic (de)hydrosilylation

Valerio Fasano, James Radcliffe, Liam Curless, Michael Ingleson

    Research output: Contribution to journalArticlepeer-review


    N−Me-Benzothiazolium salts are introduced as a new family of Lewis acids able to activate Si−H σ bonds. These carbon-centred Lewis acids were demonstrated to have comparable Lewis acidity towards hydride as found for the triarylboranes widely used in Si−H σ-bond activation. However, they display low Lewis acidity towards hard Lewis bases such as Et3PO and H2O in contrast to triarylboranes. The N−Me-benzothiazolium salts are effective catalysts for a range of hydrosilylation and dehydrosilylation reactions. Judicious selection of the C2 aryl substituent in these cations enables tuning of the steric and electronic environment around the electrophilic centre to generate more active catalysts. Finally, related benzoxazolium and benzimidazolium salts were found also to be active for Si−H bond activation and as catalysts for the hydrosilylation of imines.
    Original languageEnglish
    JournalChemistry: A European Journal
    Issue number1
    Early online date22 Nov 2016
    Publication statusPublished - 2017


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