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Issue 83, 2018
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Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides

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Abstract

The synthesis of multisubstituted pyrroles by the nickel-catalyzed reaction of N-tosyl alkynamides with arylboronic acids is reported. These reactions are triggered by alkyne arylnickelation, followed by cyclization of the resulting alkenylnickel species onto the amide. The reversible E/Z isomerization of the alkenylnickel species is critical for cyclization. This method was applied to the synthesis of pyrroles that are precursors to BODIPY derivatives and a biologically active compound.

Graphical abstract: Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides

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Publication details

The article was received on 15 Aug 2018, accepted on 21 Sep 2018 and first published on 22 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC06649C
Citation: Chem. Commun., 2018,54, 11769-11772
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    Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides

    S. M. Gillbard, C. Chung, S. N. Karad, H. Panchal, W. Lewis and H. W. Lam, Chem. Commun., 2018, 54, 11769
    DOI: 10.1039/C8CC06649C

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