Herein, we report on the tris(pentafluorophenyl)borane-catalyzed reaction of carbazole heterocycles with aryldiazoacetates. We could demonstrate that selective N-H functionalization occurs in the case of an unprotected carbazole, other N-heterocycles, and secondary amines in good yields. In contract, the protected carbazole undergoes C-H functionalization at the C-3 position in a good yield. The application of both approaches was studied in 41 examples with up to a 97% yield.