An intramolecular approach towards the regioselective construction of 2,3-diarylated indoles is reported. The reaction follows an intramolecular approach of an electrophilic N-H and C-H bond functionalization between an aniline and an acetylene. It employs the concept of a traceless tether to provide access to the free 2,2-diarylated indole products comprising a total of 18 examples. Hypervalent iodine reagents were identified as suitable promoters and four different protocols are provided including stoichiometric and catalytic transformations.