Base-Catalyzed Dehydrogenative Si-O Coupling of Dihydrosilanes: Silylene Protection of Diols

The direct dehydrogenative coupling of 1,3- and 1,4-diols and dihydrosilanes is efficiently catalyzed by Cs(2)CO(3) (10 mol%), cleanly affording six-and seven-membered 1,3-dioxo-2-silacycles with dihydrogen as the sole by-product. Conversely, 1,2-diols do not yield the expected 1,3-dioxo-2-silacyclo...

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Bibliographic Details
Published inSynlett no. 16; pp. 2482 - 2484
Main Authors Grajewska, Agnieszka, Oestreich, Martin
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
coupling
protecting groups
diols
silicon
CONVERSION
HYDROSILANES
dehydrogenation
ALKOXYSILANES
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Summary:The direct dehydrogenative coupling of 1,3- and 1,4-diols and dihydrosilanes is efficiently catalyzed by Cs(2)CO(3) (10 mol%), cleanly affording six-and seven-membered 1,3-dioxo-2-silacycles with dihydrogen as the sole by-product. Conversely, 1,2-diols do not yield the expected 1,3-dioxo-2-silacyclopentanes, essentially forming cyclic disiloxanes instead. Aside from the synthetic convenience, the procedure itself is also useful for straightforward diol derivatization prior to GLC analysis.
ISSN:0936-5214
DOI:10.1055/s-0030-1258055