New Route from Si−O to Si−C Bonds:  Alkylalkoxysilanes from Alkoxysilanes and Metal Hydrides

The typical pathway from silicon−oxygen to silicon−carbon bonds involves nucleophilic attack of an organometallic reagent on the silicon center. A new transformation from silicon−oxygen to silicon−carbon bonds is reported that proceeds without nucleophilic attack of a carbanion. The reaction of Si(OMe)4 with NaH yields MeSi(OMe)3 at temperatures above 300 °C. Mechanistic studies indicate that an intact methyl group is transferred from a methoxy group to the silicon center in the Si−C bond-forming step.