Uses
Tert-Butyldimethylsilane (t-BuMe2SiH) is widely used for the protection of hydroxy groups in sugars. Its oxidation product, tert-butyldimethylsilyl hydroperoxide (t-BuMe2SiOOH), is used for preparing luminiscent sources and prostanoids, specifically clavulons[1].
Reactions
The iridium complex [Ir(COD)(PPh3)2]+SbF6- reacts with tert-butyldimethylsilane in DMA to form [IrH2(Sol)2(PPh3)2]+SbF6-, which is an active catalyst for the regioselective di- and trisilylation of a series of representative methyl hexopyranosides, β-1,6-anhydrohexopyranosides and 1,3,5-O-methylidene inositol.The silylcarbobicyclization of 4,4-disubstituted 1,6-heptadiynes with tert-butyldimethylsilane catalyzed by Rh(acac)(CO)2, Co2Rh2(CO)12, or (t-BuNC)4RhCo(CO)4 under 50 atm of carbon monoxide gives the corresponding novel 7,7-disubstituted 2-silylbicyclo[3.3.0]octa-1,5-dien-3-ones in good yields[2-3].
References
[1] Iwao Ojima, Jiawang Zhu, Dora Fracchiolla Kass. “New and Efficient Catalytic Route to Bicyclo[3.3.0]octa-1,5-dien-3-ones.” Organometallics 15 24 (1996): 5191–5195.
[2] Mee-Kyung Chung, Marcel Schlaf. “Regioselectively Trisilylated Hexopyranosides through Homogeneously Catalyzed Silane Alcoholysis.” Journal of the American Chemical Society 127 51 (2005): 18085–18092.
[3] Iwao Ojima, Jiawang Zhu, Dora Fracchiolla Kass. “New and Efficient Catalytic Route to Bicyclo[3.3.0]octa-1,5-dien-3-ones.” Organometallics 15 24 (1996): 5191–5195.
