Categories: C-Si Bond Formation > Silanes
Synthesis of alkylsilanes
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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.
Allylsilylation allows to install both silyl and allyl groups onto a
carbon-carbon double bond directly. Proton-exchanged montmorillonite showed
excellent catalytic performances for the allylsilylation of alkenes. Isolation
of the reaction intermediate on the montmorillonite surface helped to
investigate the reaction mechanism.
K. Motokura, S. Matsunaga, A. Miyaji, Y. Sakamoto, T. Baba, Org. Lett., 2010,
12, 1508-1511.
In the presence of cationic rhodium complexes, Si-B compounds function as equivalents of nucleophilic silicon, which is
efficiently transferred onto acyclic as well as cyclic α,β-unsaturated carbonyl
compounds. [((S)-binap)Rh(cod)]ClO4 has effected an asymmetric
1,4-addition to cyclic acceptors in high enantiomeric excess.
C. Walter, G. Auer, M. Oestreich, Angew. Chem. Int. Ed., 2006, 45, 5675-5677.
A platinum-catalyzed intramolecular silaboration of borylsilanyl homoallyl
ethers gave 1-oxa-2-silacyclopentanes in high yields. The stereoselectivity of
the reactions strongly depended on the used ligands. A complementary synthesis
of a pair of diastereomers of 6-methylheptane-1,3,5-triol is described.
T. Ohmura, H. Furukawa, M. Suginome, J. Am. Chem. Soc., 2006, 128, 13366-13367.
T. Ohmura, H. Furukawa, M. Suginome, J. Am. Chem. Soc., 2006, 128, 13366-13367.
Highly efficient, stereo- and regioselective palladium-catalyzed
hydro-, sila-, and stannastannations of cyclopropenes gave multisubstituted
cyclopropylstannanes. The addition across
the double bond proceeds from the least hindered face.
M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc., 2002, 124, 11566-11567.
