Synthesis of α-Haloboronates by the Halogenation of <i>gem</i>-Diborylalkanes via Tetracoordinate Boron Species

Abstract

α-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional synthetic methods of α-haloboronates are harsh and complicated. Herein, we used ^<i>n</i>BuLi as the nucleophilic reagent to attack the boron atom in <i>gem-</i>diborylalkanes to form tetracoordinate boron species and successfully achieved α-chloroboronates and α-bromoboronates with readily accessible electrophilic halogen reagents (NCS and NBS). The reaction is transition-metal-free and features a broad substrate scope and diversified valuable products.