Abstract
AbstractReported here is the redox neutral electrochemical C(sp2)−C(sp3) cross‐coupling reaction of bench‐stable aryl halides or β‐bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench‐stable NiCl2⋅glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni‐catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β‐styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late‐stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram‐scale in a flow‐cell electrolyzer. The electrochemical C−C cross‐coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide‐spread applications in organic synthesis.
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