A one-pot protocol for the Cu(I)-catalyzed difunctionalization of indolyl ynones has been achieved via trifluoromethylation of alkyne followed by dearomatizing spirocyclization of indoles. This cascade process enables constructing diverse CF3-containing spiro[cyclopentane-1,3'-indole] scaffolds in moderate to excellent yields which have challenging quaternary spirocyclic carbon and tetrasubstituted alkenes.