Direct Synthesis of β-Amino Boronates via Amide α-C-H Bond Activation and C(sp3)-C(sp3) Coupling under Dual Ni/Photoredox Catalysis

Direct transformations of readily available amines or amides via C-H bond functionalization could provide a fast route for accessing complex molecules. While various groups have been successfully incorporated into the alpha position of the nitrogen atom with a photoredox system or C-H bond activation, couplings with functionalized alkyl halides are still very challenging. Herein, we report a direct and convenient protocol for accessing beta-amino boronates through the C(sp(3))-C(sp(3)) coupling of amides and alpha-bromoboronates. The mild conditions allow for good functional group tolerance and a broad scope. The application of the method in the late-stage modification of complex molecules further demonstrates its great potential in organic synthesis. Mechanistic studies were also conducted, and a catalytic cycle is proposed.