Categories: C-Si Bond Formation > Silanes
Synthesis of arylsilanes
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Recent Literature
A zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with
organomagnesium reagents affords a broad range of functionalized
tetraorganosilanes under mild reaction conditions. The reaction can be performed
on large scale.
K. Murakami, H. Yorimitsu, K. Oshima, J. Org. Chem., 2009,
74, 1415-1417.
Various siletanes have been used as substrates for the oxidation of
carbon-silicon bonds upon exposure to aqueous fluoride and peroxide. These
tetraalkylsilanes offer a combination of stability and reactivity with many
practical benefits, including compatibility with silicon protecting groups
and electron-rich aromatic rings.
J. D. Sunderhaus, H. Lam, G. B. Dudley, Org. Lett.,
2003, 8, 4571-4573.
A new palladium-catalyzed silylation of aryl chlorides affords desired product
in good yield, is tolerant of various functional groups, and provides access to
a wide variety of aryltrimethylsilanes from commercially available aryl
chlorides. Additionally, a one-pot procedure that converts aryl chlorides into
aryl iodides has been developed.
E. McNeill, T. E. Barder, S. L. Buchwald, Org. Lett., 2007,
9, 3785-3788.
By treatment with s-BuLi/TMEDA at -78°C, unprotected 2-methoxybenzoic
acid is deprotonated exclusively in the position ortho to the
carboxylate. A reversal of regioselectivity is observed when the acid is
treated with n-BuLi/t-BuOK.
T.-H. Nguyen, A.-S. Castanet, J. Mortier, Org. Lett.,
2006, 8, 765-768.
Related
Treatment of substituted arylbromides with tert-butyllithium in diethyl
ether at -78˚C, followed by the addition to dichlorodiethoxysilane, leads to the
quantitative formation of diaryldiethoxysilanes. Diaryldiethoxysilanes can be
reduced to the corresponding diarylsilanes by stirring with lithium aluminum
hydride in diethyl ether. This method avoids the handling of gaseous and
explosive dichlorosilane.
P. Gigier, W. A. Herrmann, F. E. Kühn, Synthesis, 2010,
1431-1432.
