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Issue 13, 2020
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Zinc triflate catalyzed 1,3-indolylation of cyclohexanones: tandem condensation, dehydrogenation and aromatization sequence

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Abstract

1,3-Bis(1-alkyl-1H-indol-3-yl)benzene derivatives have been synthesized through a Zn(OTf)2 catalyzed reaction between cyclohexanones and indoles. Cyclohexanones act as an aryl source via an alkylation–dehydrogenation–aromatization sequence, and undergo regioselective C–C bond formation with indoles at the 1,3-position. A useful library of these derivatives obtained in moderate to high yields has been prepared and a tentative mechanism has been proposed based upon GCMS analysis and time dependent NMR studies.

Graphical abstract: Zinc triflate catalyzed 1,3-indolylation of cyclohexanones: tandem condensation, dehydrogenation and aromatization sequence

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Article information


Submitted
24 Jan 2020
Accepted
03 Mar 2020
First published
05 Mar 2020

Org. Biomol. Chem., 2020,18, 2492-2500
Article type
Paper

Zinc triflate catalyzed 1,3-indolylation of cyclohexanones: tandem condensation, dehydrogenation and aromatization sequence

H. Singh, R. Tiwari, P. Sharma, P. Kumar and N. Jain, Org. Biomol. Chem., 2020, 18, 2492
DOI: 10.1039/D0OB00163E

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