A Ball Milling Enabled Cross-Electrophile Coupling

The nickel-catalyzed cross-electrophile coupling of aryl (pseudo)halides and alkyl (pseudo)halides enabled by ball-milling is herein described. Under a mechanochemical manifold, the reductive C–C bond formation was achieved in the absence of bulk solvent and air/moisture sensitive set-ups, in reaction times of 2 hours. The mechanical action provided by ball milling permits the use of a range of zinc sources to turnover the catalytic cycle of nickel. A library of 28 cross- electrophile coupled building blocks has been constructed to exemplify this technique.