The rhodium-catalyzed mono-ortho C–H activation/carbenoid insertion/aldol-type cyclization of 3-aldehyde-2-phenyl-1H-indoles with diazo compounds has been developed. This method provides a novel approach to 5H-benzo[a]carbazol-6-ols and benzo[6,7]cyclohepta[1,2-b]indol-6-ols with a broad range of substrate scope in an air atmosphere. In addition, the synthetic potentialities of the developed approach are demonstrated by gram scale and versatile late-stage transformations.