Catalytic Degradation of Aliphatic Ethers using the Lewis Superacidic Bis(perfluoropinacolato)silane

Florian S. Tschernuth, Lukas Bichlmaier, Shigeyoshi Inoue

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1 Scopus citations

Abstract

The exceptional catalytic activity of a neutral Si(IV) Lewis superacid was highlighted on the degradation of oligo- and polyethers via ring closing metathesis. Model reaction experiments with diglyme and 1,5-dimethoxypentane outlined a significantly increased reactivity surpassing comparable Lewis acid catalyst presented in the literature. The high observed activity was explained by the kinetic effect of the bulky perfluorinated substituents, blocking a second coordination site that is responsible for catalyst deactivation by substrate chelation. Further experiments with aliphatic oligoethers outlined a gradual activity loss of the catalyst due to mechanistic disparities favoring side-reactions when more than one internal product unit is present. The extraordinary affinity for the cleavage of etheric C−O bonds was ultimately demonstrated by the reaction with diethylether, producing a pentavalent silicate species that was fully characterized including SC-XRD analysis.

Original languageEnglish
Article numbere202300281
JournalChemCatChem
Volume15
Issue number11
DOIs
StatePublished - 9 Jun 2023

Keywords

  • C−O bond metathesis
  • EtO cleavage
  • Lewis acidic silanes
  • poly(ether) degradation
  • silicon catalysis

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