Direct Synthesis of β-Amino Boronates via Amide α-C–H Bond Activation and C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Coupling under Dual Ni/Photoredox Catalysis
Zihao Hu, Dong Wang, Tao Xu
Abstract
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 α 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 β-amino boronates through the C(sp 3 )–C(sp 3 ) coupling of amides and α-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.