Paper
Phenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation: synthesis of 3-hydroxy-2-oxindoles and spirooxindoles from anilides.
Published Apr 12, 2012 · Junwei Wang, Yucheng Yuan, Ruisheng Xiong
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Abstract
The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO(2)Et) in CF(3)CH(2)OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R(4))Ar) afforded the C(2)-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.
Highly CitedPhenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation can produce 3-hydroxy-2-oxindole derivatives and spirooxindoles from anilides, offering metal-free oxidative synthesis.
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