Abstract Cyclization–carbonylation–cyclizationcouplingreactions (CCC-coupling reactions) of N-propargylanilines and o-alkynylphenols catalyzed by (box)Pd(II) complexes afforded symmetrical bis(quinolin-3-yl) and bis(benzofuran-3-yl) ketones, respectively, in moderate to excellent yields. Cyclization–carbonylation–cyclizationcouplingreactions (CCC-coupling reactions) of N-propargylanilines and o-alkynylphenols