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Issue 2, 2013
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Ruthenium-catalyzed direct arylation of C–H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation

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Abstract

Arylation of ortho C–H bonds is achieved by a ruthenium-catalyzed reaction of aromatic amides having an 8-aminoquinoline moiety with aryl bromides. The reaction shows high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered C–H bonds of meta-substituted aromatic amides. Significant electronic effects are observed in Hammett plots. Electron-withdrawing groups on the aromatic amides facilitate the reaction. In contrast, both electron-donating groups and electron-withdrawing groups on aryl bromides accelerate the reaction.

Graphical abstract: Ruthenium-catalyzed direct arylation of C–H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation

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Publication details

The article was received on 12 Sep 2012, accepted on 18 Oct 2012 and first published on 18 Oct 2012


Article type: Edge Article
DOI: 10.1039/C2SC21506C
Citation: Chem. Sci., 2013,4, 664-670
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    Ruthenium-catalyzed direct arylation of C–H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation

    Y. Aihara and N. Chatani, Chem. Sci., 2013, 4, 664
    DOI: 10.1039/C2SC21506C

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