The　selective　functionalization　of　o-carboranes　is　a　popular　topic　in　carborane　chemistry.　o-Carborane　has　been　widely　used　in　aggregation-induced　luminescent　materials,　nonlinear　luminescent　materials　and　other　function　materials　due　to　its　special　3D-aromaticity.　The　pi　conjugated　systems-tethered　o-carboranes　could　further　broaden　its　applications　in　the　field　of　luminescent　materials.　Herein,　we　have　developed　a　palladium-catalyzed　Heck-type　mono-alkenylation　of　o-carboranes　featuring　phosphine　oxide　as　the　directing　group.