Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with oalkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetra substituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination