We report herein a three-component 1,2-arylboration of alkenyl amines bearing a cleavable picolinamide directing group. With aryl halides as electrophiles and B2Pin2 as nucleophiles, a wide range of alkenes could be converted into valuable boryl-functionalized aliphatic amines. The reaction proceeds with high levels of chemo- and regiocontrol and exhibits high functional group tolerance. In addition, the pinacol boronic ester group could undergo various transformations, indicating that the protocol could potentially provide a platform for versatile regioselective difunctionalization of alkenyl amines.