Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides via palladium-catalyzed intramolecular cyclization

In contrast to aromatic halides, coupling reactions involving oxidative addition of alkyl halides, especially secondary or tertiary halides, to transition metals tend to be more challenging. Herein a palladium-catalyzed intramolecular cyclization of α-bromo-propionanilides has been developed, delivering a series of 3-substituted 2-oxindoles in high yields. The method features easy to prepare starting materials, broad substrate scope and excellent functional group tolerance. A detailed mechanistic investigation has been performed.