The　catalytic　asymmetric　synthesis　of　axially　chiral　alkenes　remains　a　daunting　challenge　due　to　the　lower　rotational　barrier,　especially　for　longer　stereogenic　axis　(e.g.　C-B　axis).　The　asymmetric　radical　difunctionalization　of　alkynes　represents　an　efficient　strategy　for　these　targets.　Key　to　the　success　of　such　transformations　lies　in　aryl-stabilized　highly　reactive　alkenyl　radical　intermediates,　however,　it　remains　an　elusive　whether　a　boryl　group　could　play　a　similar　role.　Here　we　report　a　nickel-catalyzed　atroposelective　radical　relayed　reductive　coupling　reaction　of　our　designed　ethynyl-azaborines　with　simple　alkyl　and　aryl　halides　through　a　boron-stabilized　vinyl　radical　intermediate.　This　transformation　enables　a　straightforward　access　to　the　challenging　axially　chiral　alkenylborons　bearing　a　C-B　axis　in　generally　high　enantioselectivity　and　excellent　stereoselectivity.　The　catalytic　asymmetric　synthesis　of　axially　chiral　alkenes　remains　a　challenge　due　to　the　lower　rotational　barrier,　especially　for　longer　stereogenic　axis.　Here　the　authors　report　a　nickel-catalyzed　atroposelective　radical　relayed　reductive　coupling　reaction　of　ethynyl-azaborines　with　alkyl/aryl　halides　through　a　boron-stabilized　vinyl　radical　intermediate.