Abstract The reaction of 2‐alkynylanilines with phenyliodonium bis (trifluoroacetate) (PIFA) and diaryl ditellurides was found to conveniently afford the corresponding 3‐aryltelluroindoles via oxidative cyclization/tellurolation. A plausible mechanism involving the in situ formation of the reactive ArTeOCOCF 3 from the reaction of PIFA and diaryl ditellurides, and the subsequent oxidative C−N/C−Te bond formations was postulated.