Nickel-Catalyzed Tandem Cyclization of 1,6-Diynes with Indolines/Indoles through Dual C–H Bond Activation

A nickel-catalyzed site-selective tandem cyclization of 1,6-diynes with substituted indolines or indoles through consecutive dual C–H bond activation is described. In the reaction, substituted fused indole and carbazole derivatives were observed in good to excellent yields, in which three consecutiv...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-10, Vol.88 (20), p.14454-14469
Main Authors: Yadav, Suresh Kumar, Jeganmohan, Masilamani
Format: Article
Language:English
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Summary:A nickel-catalyzed site-selective tandem cyclization of 1,6-diynes with substituted indolines or indoles through consecutive dual C–H bond activation is described. In the reaction, substituted fused indole and carbazole derivatives were observed in good to excellent yields, in which three consecutive C–C bonds formed in one pot. Later, in the presence of DDQ, the aromatization of the indoline derivative was converted to the indole derivative. A possible reaction mechanism involving dual C–H bond activation as a key step was proposed to account for the present reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01463