An efficient Rh(iii)-catalyzed C-H oxidative alkylation of N-aryl-7-azaindoles with cyclopropanols by merging tandem C-H and C-C cleavage was developed. This transformation features mild reaction conditions, high regioselectivity, and excellent functional group compatibility. The resulting β-aryl ketone derivatives can be readily transformed into 7-azaindole-containing π-extended polycyclic heteroarenes.