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

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

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 C 2-symmetric or unsymmetric spirooxindoles 3. These processes feature...

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Veröffentlicht in:Organic letters 2012-05, Vol.14 (9), p.2210-2213
Hauptverfasser: Wang, Junwei, Yuan, Yucheng, Xiong, Rui, Zhang-Negrerie, Daisy, Du, Yunfei, Zhao, Kang
Format: Artikel
Sprache:eng
Schlagworte:
Anilides - chemistry
Combinatorial Chemistry Techniques
Fluoroacetates
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Oxidation-Reduction
Trifluoroacetic Acid - chemistry
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Zusammenfassung: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 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300418h