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Issue 20, 2018
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Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to p-quinone methides: efficient access to unsymmetrical diarylindolylmethanes

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Abstract

A simple, mild, efficient and chemoselective catalytic method for the straightforward synthesis of an interesting class of 2-aryl/alkyl-substituted-3-diaryl indolyl methanes in high yield is reported. This atom-efficient method proceeds via a gold-catalyzed one-pot sequential intramolecular hydroamination (C–N bond formation) of 2-alkynylanilines followed by a 1,6-conjugate addition to p-quinonemethides. The p-quinonemethides, which contain aldehyde functional groups, preferentially participate in 1,6-conjugate addition, while the aldehyde functional group remains unreactive.

Graphical abstract: Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to p-quinone methides: efficient access to unsymmetrical diarylindolylmethanes

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Publication details

The article was received on 06 Aug 2018, accepted on 12 Sep 2018 and first published on 13 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03955K
Citation: New J. Chem., 2018,42, 16886-16890
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    Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to p-quinone methides: efficient access to unsymmetrical diarylindolylmethanes

    R. Jillella, D. H. Oh and C. H. Oh, New J. Chem., 2018, 42, 16886
    DOI: 10.1039/C8NJ03955K

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