Jump to main content
Jump to site search

Issue 31, 2015
Previous Article Next Article

Reactivity of an NHC-stabilized silylene towards ketones. Formation of silicon bis-enolates vs. bis-silylation of the C[double bond, length as m-dash]O bond

Author affiliations

Abstract

The NHC-stabilized silylaminosilylene Ar(SiMe3)N(Cl)Si(IiPr) (1, Ar = 2,6-iPr2C6H3, IiPr = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene) reacted rapidly with a series of enolizable ketones under ambient conditions in a stereo- and regioselective fashion to afford silicon bis-enolates (2a–o) in high yields with the elimination of imidazolium salt. In contrast, reaction of 1 with two equivalents of benzophenone led to a slow bis-silylation of the C[double bond, length as m-dash]O double bond. All of the products have been characterized by 1H, 13C, and 29Si NMR spectroscopy and HR-MS analysis. The configurations of compounds 2h–n were determined by NOESY experiments.

Graphical abstract: Reactivity of an NHC-stabilized silylene towards ketones. Formation of silicon bis-enolates vs. bis-silylation of the C [[double bond, length as m-dash]] O bond

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Apr 2015, accepted on 26 Jun 2015 and first published on 30 Jun 2015


Article type: Paper
DOI: 10.1039/C5DT01290B
Dalton Trans., 2015,44, 14085-14091

  •   Request permissions

    Reactivity of an NHC-stabilized silylene towards ketones. Formation of silicon bis-enolates vs. bis-silylation of the C[double bond, length as m-dash]O bond

    Y. Li, B. Ma and C. Cui, Dalton Trans., 2015, 44, 14085
    DOI: 10.1039/C5DT01290B

Search articles by author

Spotlight

Advertisements