A modular approach for the synthesis of planar π-extended selenium containing molecules from selenophene has been developed. Different combinations of Pd-catalyzed desulfitative C–H bond arylations with (2-bromo)arylsulfonyl chlorides and Pd-catalyzed intra- or/and inter-molecular C–H bond arylations with aryl bromides allowed the extension of the selenophene-containing aromatic skeleton at the [b]-, [c]- or [b:d]-junctions to give phenanthro[b]selenophenes, phenanthro[c]selenophenes or diphenanthro[b:d]selenophenes.