The Formation of C-C or C-N Bonds via the Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Organosilicon Compounds: A Route to Perfluoroalkylation

The copper-catalyzed selective cleavage of alkylsilyl peroxides and the subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds are described. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to both cyclic and acyclic alkylsilyl peroxides in combination with carbon and nitrogen sources. In particular, this approach enables the facile radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Our mechanistic studies suggest that the reaction should proceed via a free-radical process.

Automated summary

The copper-catalyzed selective cleavage of alkylsilyl peroxides and subsequent formation of carbon-carbon or carbon-nitrogen bonds with organosilicon compounds is described. The reaction proceeds under mild conditions and shows a broad substrate scope, particularly suitable for radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Mechanistic studies suggest a free-radical process is involved in the reaction.