Acylsilane

File:Acylsilane.svg

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.

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Brook acylsilane synthesis scheme.

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

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Tertiary amides react with silyl lithium reagents:

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Acid chlorides are converted using hexamethyldisilane:

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

File:Kuwajima acylsilane synthesis.png

Kuwajima acylsilane synthesis, with the method to make the 1,1-bis(trimethylsilyl)alkan-1-ol.

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:

Further reading

• The reactivity of α- and β-iodo propenoylsilanes: an alternative access to polyunsaturated acylsilanes Alessandro Degl’Innocenti, Antonella Capperucci, Patrizia Scafato, Antonella Telesca Arkivoc 0-005A 2000 Article