Nickel-Catalyzed Cross-Electrophile C(sp3)–Si Coupling of Unactivated Alkyl Bromides with Vinyl Chlorosilanes

Cross-electrophile C–Si coupling has emerged as a promising tool for the construction of organosilanes, but the potential of this method remains largely unexplored. Herein, we report a C­(sp3)–Si coupling of unactivated alkyl bromides with vinyl chlorosilanes. The reaction proceeds under mild conditions, and it offers a new approach to alkylsilanes. Functionalities such as Grignard-sensitive groups (e.g., acid, amide, alcohol, ketone, and ester), acid-sensitive groups (e.g., ketal and THP protection), alkyl fluoride and chloride, aryl bromide, alkyl tosylate and mesylate, silyl ether, and amine were tolerated. Incorporation of the −Si­(vinyl)­R2 moiety into complex molecules and the immobilization of a glass surface by formed organosilanes were demonstrated.