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Issue 51, 2017
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Ruthenium(II)-catalyzed intermolecular synthesis of 2-arylindolines through C–H activation/oxidative cyclization cascade

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Abstract

Herein, we report a ruthenium-catalyzed 1,2-carboamination through C–H activation for the synthesis of 2-arylindolines from readily available, inexpensive, protected anilines and vinyl arenes. In earlier reports, indoline synthesis through C–H activation was demonstrated using sterically or electronically biased olefins suppressing β-hydride elimination. However, in the present protocol a ruthenium(II)-catalyzed indoline synthesis via interrupted Heck-type manifold with unbiased styrenes is demonstrated. Mechanistically, the reaction proceeds through pyrimidine directed electrophilic ortho metalation, alkene insertion, amine coordination, and reductive elimination to construct the indoline nucleus.

Graphical abstract: Ruthenium(ii)-catalyzed intermolecular synthesis of 2-arylindolines through C–H activation/oxidative cyclization cascade

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Publication details

The article was received on 21 Apr 2017, accepted on 30 May 2017 and first published on 30 May 2017


Article type: Communication
DOI: 10.1039/C7CC03053C
Citation: Chem. Commun., 2017,53, 6906-6909
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    Ruthenium(II)-catalyzed intermolecular synthesis of 2-arylindolines through C–H activation/oxidative cyclization cascade

    M. K. Manna, S. K. Bhunia and R. Jana, Chem. Commun., 2017, 53, 6906
    DOI: 10.1039/C7CC03053C

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