Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 10, Pages 2077-2083Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301840
Keywords
Si-H activation; Silicon; Silane transfer; Dehydrogenative coupling; Lewis acids
Categories
Funding
- Technische Universitat Berlin
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An unprecedented transfer silylation of alcohols catalyzed by the strong Lewis acid B(C6F5)(3) is described. Gaseous Me3SiH is released in situ by B(C6F5)(3)-catalyzed decomposition of 3-trimethylsilylcyclohexa-1,4-diene and subsequently reacts with an alcohol in a dehydrogenative Si-O coupling promoted by the same boron catalyst. Benzene and dihydrogen are formed during the reaction, but no salt waste is. This expedient protocol is applicable to several silicon groups, and the preparation of trimethylsilyl ethers presented here is potentially useful for alcohol derivatization prior to GLC analysis.
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