Nickel-Catalyzed Electrophilic Amination of the Biphenylene C–C σ-Bond

Abstract

A nickel-catalyzed three-component carboamination of the biphenylene C–C σ-bond has been developed. Arylboronates and hydroxylamine derivatives work as carbon nucleophiles and nitrogen electrophiles, respectively, and the corresponding difunctionalized ring-opening products are obtained in good yields. The arylboronate nucleophile can be replaced with B2pin2 (boron nucleophile) and H–Si(OMe)3 (hydride nucleophile), thus allowing for the aminoboration and hydroamination of the biphenylene C–C σ-bond under similar nickel catalysis.