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Issue 42, 2014
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An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

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Abstract

A novel molecular I2-catalyzed synthesis of isatins through C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated.

Graphical abstract: An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

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Publication details

The article was received on 24 Jul 2014, accepted on 05 Sep 2014 and first published on 08 Sep 2014


Article type: Paper
DOI: 10.1039/C4OB01564A
Citation: Org. Biomol. Chem., 2014,12, 8512-8518
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    An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

    V. Rajeshkumar, S. Chandrasekar and G. Sekar, Org. Biomol. Chem., 2014, 12, 8512
    DOI: 10.1039/C4OB01564A

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