A copper-catalyzed tandem radical cyclization of 1-(3-phenylprop-2-yn-1-yl)-1H-indole with diphenylphosphine oxides was developed. C–P bond formation was achieved coupled with C(sp2)–H functionalization. It provided an access to construct the pyrrolo[1,2-a]indole motif and a series of 2-phosphinoyl-9H-pyrrolo[1,2-a]indoles.