The palladium-catalyzed intramolecular oxidative C-H/C-H coupling of 2-aryloxypyridines as challenging substrates is investigated to construct an important class of N,O-mixed heteroacenes, i.e. benzofuropyridines. It is found that 2,6-diaryloxypyridines efficiently undergo double cyclization to provide bisbenzofuro[2,3-b:3',2'-e]pyridines of interest in materials chemistry.