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Issue 63, 2016
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The amide C–N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C–H activation and annulation reactions: access to 8-amido isocoumarins

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Abstract

The N–O, N–N and O–O bonds are the frequently used internally oxidative directing groups used in various redox-neutral coupling reactions. The sole use of the C–N bond as the oxidizing directing group was reported recently by Li X. and co-workers for the Rh(III)-catalyzed C–H activation of phenacyl ammonium salts. Herein, we report the use of the amide C–N bond of isatins as the oxidizing directing group for the Ru(II)-catalyzed redox-neutral C–H activation and annulation reactions with alkynes which afford 8-amido isocoumarins. The reaction also features excellent regioselectivity with alkyl aryl substituted alkynes.

Graphical abstract: The amide C–N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C–H activation and annulation reactions: access to 8-amido isocoumarins

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Publication details

The article was received on 27 May 2016, accepted on 06 Jul 2016 and first published on 11 Jul 2016


Article type: Communication
DOI: 10.1039/C6CC04461A
Citation: Chem. Commun., 2016,52, 9809-9812
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    The amide C–N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C–H activation and annulation reactions: access to 8-amido isocoumarins

    P. P. Kaishap, B. Sarma and S. Gogoi, Chem. Commun., 2016, 52, 9809
    DOI: 10.1039/C6CC04461A

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