Issue 50, 2016

The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination

Abstract

A novel one-pot tandem reaction of indole and β-carbonyl nitrile to generate dicarbonyl indoles has been developed. This tandem process involves α-oxonation of the β-carbonyl nitrile to afford α,β-dicarbonyl nitrile, Friedel–Crafts reaction with indoles and subsequent retro-cyanohydrination of cyano tertiary alcohol form dicarbonyl indoles.

Graphical abstract: The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination

Supplementary files

Article information

Article type
Communication
Submitted
14 feb 2016
Accepted
27 apr 2016
First published
28 apr 2016

RSC Adv., 2016,6, 44029-44033

The dicarbonylation of indoles via Friedel–Crafts reaction with dicarbonyl nitrile generated in situ and retro-cyanohydrination

J. Yan, G. He, F. Yan, J. Zhang and G. Zhang, RSC Adv., 2016, 6, 44029 DOI: 10.1039/C6RA04016K

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