Phenylsilane
- 1 min read
- 2 chapters
Related on Lably
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.
- 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
Sign in to keep reading
One more chapter is free with a Lably account.
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.
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.
Phenylsilane has been used as a hydride donor in synthetic enzymes.