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Issue 31, 2015
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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

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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

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Article information


Submitted
03 Apr 2015
Accepted
26 Jun 2015
First published
30 Jun 2015

Dalton Trans., 2015,44, 14085-14091
Article type
Paper

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

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