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Triethylsilane

75 hPa at 38 °C 126 hPa at 50 °C

Triethylsilane , also known as TES or triethylsilicon hydride, is the organosilicon compound with the formula (C2H5)3SiH. It is a trialkylsilane. The Si-H bond is reactive.

It was first discovered by Albert Ladenburg in 1872 among the products of reduction of tetraethyl orthosilicate with sodium and diethylzinc. He also prepared it by a stepwise reduction via ethoxytriethylsilane and named it silicoheptyl hydride, reflecting the idea of a silicon compound analogous to a seven-carbon hydrocarbon. This colorless liquid finds occasion use in organic synthesis. As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.

Organic chemistry

Triethylsilane is an occasional reagent in organic synthesis. In combination with indium compounds, it reduces esters to ethers. The reaction is typically performed in chloroform at 60 °C, using 0.05 equivalents of InBr3 catalyst. This system can also accommodate other carbonyl compounds like tertiary amides and carboxylic acids.

Additional reading

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References

References

  1. {{Sigma-Aldrich
  2. Ladenburg, A.. (1872). "Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate". Justus Liebigs Annalen der Chemie.
  3. (2007). "Encyclopedia of Reagents for Organic Synthesis".
  4. (1993). "Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway". Journal of the American Chemical Society.
  5. (November 2008). "Direct Reduction of Esters to Ethers with an Indium(III) Bromide/Triethylsilane Catalytic System". Synthesis.
  6. "Synthesis of Ethers from Carbonyl Compounds by Reductive Etherification Catalyzed by Iron(III) and Silyl Chloride".
  7. "An Efficient One-Pot Synthesis of Unsymmetrical Ethers: A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System".
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reducing-agents carbosilanes
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