Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides
2012
Wang, Junwei | Yuan, Yucheng | Xiong, Rui | Zhang-Negrerie, Daisy | Du, Yunfei | Zhao, Kang
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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