An iridium-catalyzed direct C-7 selective C-H alkynylation of indolines at room temperature, for the first time, has been developed via C-H bond activation. Furthermore, the first example of direct C-H alkynylation of carbazoles at the C1 position is also achieved. More importantly, the resulting product can be readily transformed into C7-alkynylated indoles, further widening the C-7 derivatization of indoles and highlighting the synthetic utility of this methodology.