The use of Me3SiO(-)/Bu4N(+) as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
Funding
European Research Association ERA-Chemistry and the Irish Research Council (IRC).
Das M, O'Shea DF. Bu4N(+) Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes. Journal of Organic chemistry. 2014;79(12):5595-607.