Carbazoles are ubiquitous N-heterocycles used throughout medicinal chemistry and the material sciences. From a pharmaceutical perspective, the carbazole core features extensively in drugs and natural products, many of which exhibit potent anti-proliferative activities (Figure ). The breadth of applications has inspired the development of numerous methodologies for their preparation. Pd-catalyzed processes in particular enable a [3+2]heteroannulation via a Pd(0)-catalyzed Buchwald-Hartwig amination, followed by a Pd(II)-catalyzed C-arylation at a late stage in a synthetic workflow. However, a generalized set of guidelines outlining the molecular determinants which define the chemo-and regioselective control of each C-N/C-C bondforming reaction, and the factors which influence Pd(0) versus Pd(II) catalysis in a one-pot process has not been established. This is an important requirement for the formation of tetracyclic carbazoles where a regioselective C-H activation step is required. In this manuscript, we establish reaction guidelines to prepare tri-and tetracyclic carbazoles by controlling the chemoselectivity of the first Pd(0)-catalyzed C-N bondforming step, and the regioselectivity of the second Pd(II)catalyzed C/N-arylation (Figure ). Our rationale was to use chloroanilines (1) to define the A-ring of a carbazole core, and heteroaryl bromides to form the C/D-rings of tricyclic and tetracyclic products.