Ni-catalyzed reductive alkylgermylation of activated alkenes: Modular access to polyfunctionalized alkyl germanes

Organogermanium compounds have played a significant role in organic synthesis, drug discovery, and materials science. The efficient access to different types of organogermanium compounds is of greatest importance for the exploration and acceleration of their further applications. However, a comprehensive study of the practical and modular construction of various substituted alkyl germanes (i.e., three-dimensional frameworks), with a diverse functionality, still remains rare. We have in the present study reported on a highly efficient nickel-catalyzed reductive alkylgermylation of activated alkenes by using a variety of functionalized alkyl halides including unactivated alkyl bromides (1°, 2°, 3°) and activated benzyl/allyl chlorides, with commercially available chlorogermanes. A wide array of diversely substituted alkyl germanes has been achieved in high modularity and efficiency under elementary and mild reaction conditions. Furthermore, by using this method, the successful functionalization of drug molecules demonstrates its practicability and utility.