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Acylsilane

Class of chemical compounds

Acylsilane

Class of chemical compounds

The general structure of an acylsilane

Acylsilanes are a group of chemical compounds sharing a common functional group with the general structure RC(O)-SiR3.

Synthesis

Acylsilanes can be synthesized by treating acyl anion equivalents with silyl halides (typically trimethylsilyl chloride, tmsCl). Silylation of 2-lithio-1,3-dithiane, followed by hydrolysis of the dithioacetal group with mercury(II) chloride. Analogous methods has also been used to produce acylgermanes.

Brook acylsilane synthesis scheme.

Several approaches to acylsilanes start with carboxylic acid derivatives. Esters undergo reductive silylation en route to acylsilanes: : :

Tertiary amides react with silyl lithium reagents: :

Acid chlorides are converted using hexamethyldisilane: :

Some acyl silanes are prepared by oxidation of a suitable silanes.

Reactions

Acylsilanes are starting compounds in the Brook rearrangement with vinyl lithium compounds to silyl enol ethers.

Acyl silanes and aryl bromides are coupling partners in Pd-catalyzed cross coupling reactions:

References

References

  1. (2013). "Acylsilanes: Valuable Organosilicon Reagents in Organic Synthesis". Chemical Society Reviews.
  2. Brook, A. G.. (Jan 1, 1967). "Synthesis of Silyl and Germyl Ketones". Journal of the American Chemical Society.
  3. (1976-09-05). "An Efficient Method for the Preparation of Acylsilane and α-haloacylsilane". Chemistry Letters.
  4. (2021). "Palladium-Catalyzed Acetylation of Arylbromides". Organic Syntheses.
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functional-groups organosilicon-compounds
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