Palladium-Catalyzed Three-Component Reaction of Dihydrosilanes and Vinyl Iodides in the Presence of Alcohols: Rapid Assembly of Silyl Ethers of Tertiary Silanes.

ABSTRACT

A one-pot reaction that directly converts dihydrosilanes into silyl ethers of tertiary silanes is reported. Under palladium catalysis, one Si-H bond of the dihydrosilane formally engages in C(sp3 )-Si bond formation with a vinyl iodide while the other Si-H bond is transformed into a silyl iodide that undergoes facile alcoholysis with an alcohol. The C-C double bond is reduced in that process. This three-component reaction provides in a single synthetic operation an access to silyl ethers of functionalized and hindered alcohols. Several of those would otherwise be difficult to make but the intermediacy of a highly reactive silyl iodide even allows for tert-butanol to react at room temperature.