Chemistry:Triethylsilane
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.[1] 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.[2] As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis.[3]
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.[4][5] This system can also accommodate other carbonyl compounds like tertiary amides and carboxylic acids.[6]
Additional reading
- Richard T. Beresis, Jason S. Solomon, Michael G. Yang, Nareshkumar F. Jain, and James S. Panek (1998). "Synthesis of Chiral (E)-Crotylsilanes: [3R- AND 3S-]-(4E)-Methyl 3-(Dimethylphenylsilyl)-4-Hexenoate ". Organic Syntheses 75: 78. http://www.orgsyn.org/demo.aspx?prep=v75p0078.
- Alessandro Dondoni and Daniela Perrone (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2-[(4S)-N-tert-Butoxycarbonyl-2,2-Dimethyl-1,3,-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde ". Organic Syntheses 77: 78. http://www.orgsyn.org/demo.aspx?prep=v77p0078.
- Pape C. (1881). "Über Siliziumpropylverbindungen". Ber 14: 1873. http://gallica.bnf.fr/ark:/12148/bpt6k906939/f283.chemindefer.
- Charles A. Kraus; Walter K. Nelson (1934). "The Chemistry of the Triethylsilicyl Group". J. Am. Chem. Soc. 56 (1): 195–202. doi:10.1021/ja01316a062. Bibcode: 1934JAChS..56..195K.
References
- ↑ Ladenburg, A. (1872). "Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate" (in de). Justus Liebigs Annalen der Chemie 164 (2): 300–332. doi:10.1002/jlac.18721640212. ISSN 0075-4617. https://books.google.com/books?id=HNXyAAAAMAAJ&pg=RA2-PA300.
- ↑ Fry, James L.; Rahaim, Ronald J.; Maleczka, Robert E. (2007). "Triethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rt226.pub2. ISBN 978-0471936237.
- ↑ Brookhart, M.; Grant, B. E. (1993). "Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: Direct evidence for a silyl migration pathway". Journal of the American Chemical Society 115 (6): 2151–2156. doi:10.1021/ja00059a008. Bibcode: 1993JAChS.115.2151B.
- ↑ Sakai, Norio; Moriya, Toshimitsu; Fujii, Kohji; Konakahara, Takeo (November 2008). "Direct Reduction of Esters to Ethers with an Indium(III) Bromide/Triethylsilane Catalytic System" (in en). Synthesis 2008 (21): 3533–3536. doi:10.1055/s-0028-1083191. ISSN 0039-7881. http://www.thieme-connect.de/DOI/DOI?10.1055/s-0028-1083191.
- ↑ "Synthesis of Ethers from Carbonyl Compounds by Reductive Etherification Catalyzed by Iron(III) and Silyl Chloride". https://www.organic-chemistry.org/abstracts/lit4/995.shtm.
- ↑ "An Efficient One-Pot Synthesis of Unsymmetrical Ethers: A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System". https://www.organic-chemistry.org/abstracts/lit1/800.shtm.
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