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.