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

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 hydroami...

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Bibliographic Details
Published in:New journal of chemistry 2018, Vol.42 (20), p.16886-16890
Main Authors: Jillella, Raveendra, Oh, Dong hwan, Oh, Chang Ho
Format: Article
Language:English
Subjects:
Aromatic compounds
Cascade chemical reactions
Catalysis
Chemical synthesis
Conjugates
Functional groups
Gold
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ03955K