Categories: C-Si Bond Formation > Silanes
Synthesis of allylsilanes
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A palladium-catalyzed allylic silylation using allylic alcohols and disilanes as
precursors proceeds smoothly under mild and neutral conditions and is suitable
for synthesis of regio- and stereodefined allylsilanes. The presented silylation
reaction can be easily extended to include synthesis of allylboronates by change
of the dimetallic reagent.
N. Selander, J. R. Paasch, K. J. Szabó, J. Am. Chem. Soc., 2011,
133, 17701-17703.
An open-bent titanocene complex [Me2C(C5H4)2TiMe2]
proved to be efficient for the hydrosilylation of a variety of substrates such
as disubstituted dienes, activated alkenes, and even an alkyne.
R. Pop, J. L. Cui, L. Adriaenssens, V. Comte, P. Le Gendre, Synlett, 2011,
679-683.
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.
Pd-catalyzed silylation of allylic phenyl ethers as electrophiles with
organodisilanes can be run at room temperature in water as the only medium using
micellar catalysis.
R. Moser, T. Nishikata, B. H. Lipshutz, Org. Lett., 2010,
12, 28-31.
A new method for the synthesis of substituted 2-acylallylmetal reagents in a
highly regio- and stereoselective fashion involving a three-component assembly
of allenes, acyl chlorides, and bimetallic reagents (B-B, Si-Si, and Sn-Sn)
catalyzed by phosphine-free palladium complexes is described.
F.-Y. Yang, M. Shanmugasundaram, S.-Y. Chuang, P.-J. Ku, M.-Y. Wu, C.-H. Cheng,
J. Am. Chem. Soc.,
2003, 125, 12576-12583.
An enantioselective silaboration of allenes was achieved using an achiral
silylborane in the presence of a palladium catalyst bearing a chiral
monodentate phosphine ligand. The enantioselectivity depended on the
bulkiness of substituents of allenes.
T. Ohmura, H. Taniguchi, M. Suginome, J. Am. Chem. Soc., 2006, 128, 13682-13683.
