A cobalt–Xantphos complex catalyzes the addition of an arylzinc reagent to an unactivated internal alkyne; the reaction most likely involves insertion of the alkyne into an arylcobalt species and vinyl‐to‐aryl 1,4‐cobalt migration, followed by transmetalation with the arylzinc reagent. Interception of the resulting ortho ‐alkenylarylzinc species with electrophiles allows access to 1‐alkenyl arenes functionalized in the 2‐position.