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A highly diastereoselective, atom-economical, and palladium-catalyzed Heck protocol for the assembly of structurally diverse indoline scaffolds with vicinal tertiary as well as quaternary stereocenters is described, starting from readily available N-halobenzoyl o-haloaniline derivatives and phenylboronic acids. This cascade annulation reaction, which is scalable and conducts under an ambient atmosphere, provides the valuable tetracyclic indoline derivatives in an efficient and straightforward way.