Arylsilylation of Electron-Deficient Alkenes via Cooperative Photoredox and Nickel Catalysis

Carbosilylation of alkenes can be an efficient approach
to the
synthesis of organosilicon compounds. However, few general methods
of carbosilylation are known. Here, we introduce a strategy for arylsilylation
of electron-deficient terminal alkenes by combining photoredox-catalyzed
silyl radical generation, innate reactivity of silyl radical with
alkene, and Ni-catalyzed aryl-alkyl cross-coupling. This cooperative
photoredox and nickel catalysis operates under mild conditions. It
employs readily available alkenes, aryl bromides, and silane as reagents,
and it produces useful synthetic building blocks in a modular manner.