The regioselective C–H bond cleavage/C–O bond formation takes place smoothly upon treatment of 9-(pyridin-2-yl)carbazoles with acetic acid in the presence of a silver salt oxidant under ruthenium catalysis to afford the corresponding C1- and C8-diacetoxylated products. Under similar conditions, the acetoxylation of 2-aryl-1-(pyridin-2-yl)indoles as well as 1-aryl-7-azaindoles can also be conducted efficiently.