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An efficient Rh(III)-catalyzed C–H alkenylation/directing group migration cascade between indoles and alkynes for the assembly of tetrasubstituted alkenes is reported. The carbamoyl directing group migrates to the carbon of the alkene moiety of the products through rare Rh-catalyzed C–N bond cleavage after the C–H alkenylation step and thus acts as an internal amidation reagent. This protocol shows broad substrate scope, excellent regio/stereoselectivity, and good to excellent yields.