Spirosilane derivatives have been investigated as fluoride sensors. The reactions between these compounds and different fluoride sources, which resulted in structural alterations, have been monitored and quantified by UV and fluorescence spectroscopy. The high selectivity of these probes for fluoride ions has been demonstrated in either organic or aqueous media.
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Photocatalytic C-Si Bond Formations Using Pentacoordinate Silylsilicates as Silyl Radical Precursors: Synthetic Tricks Using Old Reagents.
Org Lett
March 2023
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.
A visible-light-induced photocatalytic C-Si formation strategy has been disclosed by uncovering the reactivity of Martin's spirosilane-derived pentacoordinate silylsilicates as silyl radical precursors. The hydrosilylation of a broad spectrum of alkenes and alkynes, as well as the C-H silylation of heteroarenes, has been demonstrated. Remarkably, Martin's spirosilane was stable and could be recovered via a simple workup process.
View Article and Find Full Text PDFSynthesis and Reactivity of Martin's Spirosilane-Derived Chloromethylsilicate.
Molecules
March 2022
CNRS, Institut Parisien de Chimie Moléculaire, IPCM, Sorbonne Université, 4 Place Jussieu, F-75005 Paris, France.
Pentacoordinate silicon derivatives with a chloromethyl ligand are versatile compounds that are usually obtained from the corresponding tetravalent trialkoxy- or trihalogeno(chloromethyl)silane. We describe herein the synthesis of a chloromethylsilicate bearing two Martin's ligands readily obtained by addition of in situ generated chloromethyllithium to a spirosilane. The reactivity of this new species was evaluated and it has been established that the chloride is displaced by strong nucleophiles such as alkyllithiums and (hetero)aryllithiums.
View Article and Find Full Text PDFA Parisian Vision of the Chemistry of Hypercoordinated Silicon Derivatives.
Chem Rec
May 2021
Institut Parisien de Chimie Moléculaire, Sorbonne Université, CNRS, 4 place Jussieu, 75005, Paris.
Less than ten years of acquaintance with hypercoordinated silicon derivatives in our lab is described in this account. Martin's spirosilane derivatives open new opportunities as ligands and as agents for the activation of small molecules and bis-catecholato silicates have proven to be exquisite radical precursors in photoredox conditions for broad synthetic applications.
View Article and Find Full Text PDFInteraction between Spirosilanes and Lewis Bases: from Coordination to Frustration.
Chemistry
July 2019
CNRS, Institut Parisien de Chimie Moléculaire, Sorbonne Universite, 4 Place Jussieu, CC 229, 75252, Paris Cedex 05, France.
In this work, the interaction between Lewis bases, especially N-heterocyclic carbenes (NHCs), and hindered neutral silicon derivatives featuring high Lewis acidity is described. The formation of normal and abnormal Lewis adducts could be controlled by varying the acidity of the corresponding tetravalent spiro organosilane. Some DFT calculations permitted to gain insight into the thermodynamics of the NHC-spirosilane interaction featuring various NHCs differing in size and σ-donor capacity.
View Article and Find Full Text PDFVersatile access to Martin's spirosilanes and their hypervalent derivatives.
J Org Chem
March 2015
‡Sorbonne Universités UPMC Universite Paris 06, UMR CNRS 8232, Institut Parisien de Chimie Moléculaire, 4 place Jussieu, CC 229, F-75005 Paris, France.
A new route to Martin's spirosilanes has been devised. The original synthesis does not allow diversely substituted spirosilane derivatives to be synthesized, and thus their corresponding silicates. In this report, Martin's spirosilanes bearing alkyl, aryl, halogen, alkoxy, and trifluoromethyl substituents on the aryl ring have been prepared through a versatile four-step route.
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