Silane, tetramethyl-, zinc complex

Physical properties

colorless liquid; mp ?80°C; bp 44°C/1.5 Torr; d 1.08 g cm?3.

The Uses of Silane, tetramethyl-, zinc complex

Bis[(trimethylsilyl)methyl]zinc is a useful organometallic reagent for organic synthesis.
Bis[(trimethylsilyl)methyl]zinc has proven to be a useful nucleophile in transition metal-catalyzed cross-coupling reactions with, for example, alkenyl sulfoximines (eq 1).

Preparation

several methods for the preparation of bis[(trimethylsilyl)methyl]zinc have been reported.Addition of powdered anhydrous zinc(II) chloride to a solution of [(trimethylsilyl)methyl]magnesium chloride in diethyl ether at 0°C and subsequent stirring for 4 days at room temperature affords the title compound in 90% yield after fractional distillation. A second route consists of the reaction of (iodomethyl)trimethylsilane with zinc/copper couple(prepared by reduction of CuO with dihydrogen in the presence of zinc dust) at reflux for 3 h and affords the title compound in 56% yield. Bis[(trimethylsilyl)methyl]zinc can also be prepared quantitatively by reacting bis[(trimethylsilyl)methyl]mercury with an excess of zinc at ambient conditions.