Preparation of Substituted Tetrahydroisoquinolines by Pd(II)-Catalyzed NH₂‑Directed Insertion of Michael Acceptors into C–H Bonds Followed by NH₂‑Conjugated Addition

3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag₂CO₃ as an oxidant. Presumably, activation of an ortho C–H bond of the aromatic ring with Pd­(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.