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4.4.40.7.1 Variation 1: From Vinyl Halides with [(Trimethylsilyl)methyl]magnesium Halides and Related Species

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024846.

The coupling of a vinyl halide with [(trimethylsilyl)methyl]magnesium halide in the presence of a nickel or palladium catalyst provides allylsilanes in good yield with excellent control of regio- and stereoselectivity, for example, the preparation of silanes 29, 30, and 31 (Scheme 15).[‌80‌,‌81‌] This is a straightforward route to allylsilanes if the corresponding vinyl halides are readily available. The stereochemical purity of the starting material is critical for the formation of an isomerically pure allylsilane. The asymmetric version of this reaction has been achieved in the presence of a ferrocene-based chiral palladium catalyst; this has led, for example, to the formation of chiral silane 32 (Scheme 15).[‌83‌]

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