Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

Wang, Junwei; Yuan, Yucheng; Xiong, Rui; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang

Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

2012

The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO₂Et) in CF₃CH₂OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1′ (E = CON(R⁴)Ar) afforded the C₂-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp²)–C(sp³) bond formation, followed by oxidative hydroxylation or spirocyclization.

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