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Phenylsilane
Chemical compound From Wikipedia, the free encyclopedia
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Phenylsilane, also known as silylbenzene, a colorless liquid, is one of the simplest organosilanes with the formula C6H5SiH3. It is structurally related to toluene, with a silyl group replacing the methyl group. Both of these compounds have similar densities and boiling points due to these similarities. Phenylsilane is soluble in organic solvents.
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Synthesis and reactions
Phenylsilane is produced in two steps from Si(OEt)4. In the first step, phenylmagnesium bromide is added to form Ph−Si(OEt)3 via a Grignard reaction. Reduction of the resulting Ph−Si(OEt)3 product with LiAlH4 affords phenylsilane.[2]
- Ph−MgBr + Si(OEt)4 → Ph−Si(OEt)3 + MgBr(OEt)
- 4 Ph−Si(OEt)3 + 3 LiAlH4 → 4 Ph−SiH3 + 3 LiAl(OEt)4
Uses
Phenylsilane can be used to reduce tertiary phosphine oxides to the corresponding tertiary phosphine.
- P(CH3)3O + PhSiH3 → P(CH3)3 + PhSiH2OH
The use of phenylsilane proceeds with retention of configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines.[3]
Phenylsilane combines with caesium fluoride to give the ate complex [PhSiFH3]−. This species functions as a hydride donor, reducing 4-oxazolium salts to 4-oxazolines.[4]
Phenylsilane has been used as a hydride donor in synthetic enzymes.[5]
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References
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