A hypervalent iodine-mediated intermolecular α-umpolung reaction between α-aryl- or alkyl-substituted amides and benzotriazoles or purine derivatives as N -centered nucleophiles has been established. The reaction involves sequential intra/intermolecular oxidative C-N couplings in a controlled manner, affording tetrasubstituted 3,3'-oxindoles in moderate to good yields. This approach efficiently addresses the challenges in constructing tetrasubstituted carbon centers via α-umpolung functionalizations of carbonyl compounds and serves as a new strategy for synthesizing biologically important 3,3'-disubstituted oxindoles.