An Isolable Silicon Analogue of a Ketone that Contains an Unperturbed Si=O Double Bond

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22 Citations (Scopus)

Abstract

Despite tremendous efforts to synthesize isolable compounds with an Si=O bond, silicon analogues of ketones that contain an unperturbed Si=O bond have remained elusive for more than 100 years. Herein, we report the synthesis of an isolable silicon analogue of a ketone that exhibits a three-coordinate silicon center and an unperturbed Si=O bond, thus representing the first example of a genuine silanone. Most importantly, this silanone does not require coordination by Lewis bases and acids and/or the introduction of electron-donating groups to stabilize the Si=O bond. The structure and properties of this unperturbed Si=O bond were examined by a single-crystal X-ray diffraction analysis, NMR spectroscopy, and theoretical calculations. Bimolecular reactions revealed high electrophilicity on the Si atom and high nucleophilicity on the O atom of this genuine Si=O bond.

Original languageEnglish
Pages (from-to)9425-9428
Number of pages4
JournalAngewandte Chemie - International Edition
Volume58
Issue number28
DOIs
Publication statusPublished - 2019 Jul 8

Keywords

  • Si=O bonds
  • carbonyl compounds
  • ketones
  • silanones
  • silicon

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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