Pd-Catalyzed Intramolecular Cyclization of 2-Iodoanilino Esters to Dihydroquinolin-4-ones

Significance

A palladium-catalyzed intramolecular cyclization of β-(2-iodoanilino)esters A to give dihydroquinolin-4-ones B is reported. K₃PO₄ along with Et₃N in toluene was found to be the effective combination for the intramolecular condensation, although under these conditions small amounts of hydrodehalogenation product C were detected in some cases. Carbamate (R² = CO₂Me) and sulfonamide (R² = Ts) failed to undergo cyclization and only gave reduced product C.