N-Methyl-Benzothiazolium Salts as Carbon Lewis Acids for Si−H σ-Bond Activation and Catalytic (De)hydrosilylation

Valerio Fasano, James E. Radcliffe, Liam D. Curless, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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
Pages (from-to)187-193
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number1
Early online date25 Oct 2016
DOIs
Publication statusE-pub ahead of print - 25 Oct 2016

Keywords

  • benzothiazolium salts
  • frustrated Lewis pairs
  • hydrosilylation
  • Lewis acids
  • organocatalysis

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