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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
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Cyclic (Amino)(Phosphonium Bora-Ylide)Silanone: A Remarkable Room-Temperature-Persistent Silanone
Alfredo Rosas-Sánchez1, Isabel Alvarado-Beltran1, Antoine Baceiredo1
1Université de Toulouse, UPS, and CNRS, LHFA UMR 5069 (Equipe-ECOIH), 118 route de Narbonne, 31062, Toulouse, France.
Angewandte Chemie (International Ed. in English)
|October 28, 2017
Summary
A novel silanone featuring a phosphonium bora-ylide group shows dramatically extended room-temperature stability (4 days). This enhanced stability allows for easier handling and broader applications in silicon chemistry.
Area of Science:
- Organosilicon Chemistry
- Main Group Chemistry
- Supramolecular Chemistry
Background:
- Silanones are reactive silicon-oxygen compounds.
- Stabilizing silanones is crucial for their synthetic utility.
- Previous silanone derivatives exhibited limited room-temperature stability.
Purpose of the Study:
- To synthesize and characterize a novel silanone with enhanced stability.
- To investigate the influence of bulky substituents on silanone reactivity.
- To explore the potential of stabilized silanones as precursors for new silicon compounds.
Main Methods:
- Crystalline isolation of the target silanone.
- Spectroscopic characterization (NMR, IR, etc.).
- Stability studies at room temperature and in the presence of Lewis acids.
Main Results:
- A silanone substituted with amino and phosphonium bora-ylide groups was successfully isolated in crystalline form.
- The phosphonium bora-ylide substituent significantly extended the silanone's room-temperature lifetime to 4 days, a substantial improvement over related compounds (5 hours).
- Complexation with magnesium bromide (MgBr2) further enhanced the silanone's stability, preventing degradation for over 3 weeks at room temperature.
Conclusions:
- Bulky phosphonium bora-ylide substituents can dramatically enhance the stability of silanones.
- The stabilized silanone is a valuable precursor for synthesizing novel silicon-containing compounds.
- Lewis acid complexation offers an additional strategy for stabilizing reactive silanone intermediates.
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