The　direct　C-H　functionalization　of　1,2-benzazaborines,　especially　asymmetric　version,　remains　a　great　challenge.　Here　we　report　a　palladium-catalyzed　enantioselective　C-H　olefination　and　allylation　reactions　of　1,2-benzazaborines.　This　asymmetric　approach　is　a　kinetic　resolution　(KR),　providing　various　C-B　axially　chiral　2-aryl-1,2-benzazaborines　and　3-substituted　2-aryl-1,2-benzazaborines　in　generally　high　yields　with　excellent　enantioselectivities　(selectivity　(S)　factor　up　to　354).　The　synthetic　potential　of　this　reaction　is　showcased　by　late-stage　modification　of　complex　molecules,　scale-up　reaction,　and　applications.　A　palladium-catalyzed　enantioselective　C-H　olefination　and　allylation　reactions　of　1,2-benzazaborines　was　developed,　which　allows　to　achieve　a　kinetic　resolution　of　2-aryl-1,2-benzazaborines　representing　a　straightforward　route　to　construct　C-B　axial　chirality.　Two　kinds　of　C-B　axially　chiral　2-aryl-1,2-benzazaborines　are　then　readily　diversified　into　a　range　of　chiral　intermediates,　as　well　as　transformed　into　potential　chiral　ligand.image