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Issue 3, 2014
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Ylide mediated carbonyl homologations for the preparation of isatin derivatives

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Abstract

An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N–H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.

Graphical abstract: Ylide mediated carbonyl homologations for the preparation of isatin derivatives

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Publication details

The article was received on 10 Oct 2013, accepted on 08 Nov 2013 and first published on 27 Nov 2013


Article type: Communication
DOI: 10.1039/C3OB42024H
Citation: Org. Biomol. Chem., 2014,12, 406-409
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    Ylide mediated carbonyl homologations for the preparation of isatin derivatives

    C. T. Lollar, K. M. Krenek, K. J. Bruemmer and A. R. Lippert, Org. Biomol. Chem., 2014, 12, 406
    DOI: 10.1039/C3OB42024H

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