Issue 2, 2024

Organocatalytic Friedel–Crafts arylation of aldehydes with indoles utilizing N-heterocyclic iod(az)olium salts as halogen-bonding catalysts

Abstract

The Friedel–Crafts arylation is among the most known organic reactions, usually being promoted by a Lewis acid, that have been employed for the synthesis of bis-indolyl methanes. Herein, we report a mild, inexpensive, green and organocatalytic protocol for the promotion of a Friedel–Crafts-type reaction between indoles and aldehydes, where N-heterocyclic iod(az)olium salts are utilized as halogen-bonding catalysts, leading to the double addition of the indole motif. A variety of aliphatic and aromatic aldehydes were converted into diarylmethanes in good to high yields, while the scope of indoles was also investigated. Water was employed as the solvent, while the reaction time was short. The reaction mechanism was also studied.

Graphical abstract: Organocatalytic Friedel–Crafts arylation of aldehydes with indoles utilizing N-heterocyclic iod(az)olium salts as halogen-bonding catalysts

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Article information

Article type
Paper
Submitted
28 Sep 2023
Accepted
13 Nov 2023
First published
15 Nov 2023
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2024,26, 825-831

Organocatalytic Friedel–Crafts arylation of aldehydes with indoles utilizing N-heterocyclic iod(az)olium salts as halogen-bonding catalysts

E. M. Galathri, T. J. Kuczmera, B. J. Nachtsheim and C. G. Kokotos, Green Chem., 2024, 26, 825 DOI: 10.1039/D3GC03687A

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