Issue 9, 2011
From the journal:

Green Chemistry

Nanoporous aluminosilicate catalyzed Friedel–Crafts alkylation reactions of indoles with aldehydes and acetals†

Tomasz M. Kubczyk,a   Sarah M. Williams,a   Jacqueline R. Kean,a   Thomas E. Davies,b   Stuart H. Taylorb  and  Andrew E. Graham*a  

* Corresponding authors

a Sustainable Environment Research Centre (SERC), Department of Science and Sport, University of Glamorgan, Pontypridd, UK

b Cardiff Catalyst Institute, School of Chemistry, Cardiff University, Park Place, Cardiff, UK

Abstract

Nanoporous aluminosilicate materials efficiently catalyze Friedel–Crafts reactions of indoles to produce bisindolylalkane products. These reactions proceed rapidly and in high yields when acetals are used in place of the more commonly used carbonyl reagents. It is possible to capitalise on the large difference in the rates of reaction observed with aldehydes and acetals to develop a tandem acetalization-Friedel–Crafts protocol in which the acetal is generated in situ and undergoes subsequent reaction.

Graphical abstract: Nanoporous aluminosilicate catalyzed Friedel–Crafts alkylation reactions of indoles with aldehydes and acetals

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Article information

DOI
https://doi.org/10.1039/C1GC15669A
Article type
Communication
Submitted
07 Jun 2011
Accepted
12 Jul 2011
First published
25 Jul 2011

Green Chem., 2011,13, 2320-2325

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Nanoporous aluminosilicate catalyzed Friedel–Crafts alkylation reactions of indoles with aldehydes and acetals

T. M. Kubczyk, S. M. Williams, J. R. Kean, T. E. Davies, S. H. Taylor and A. E. Graham, Green Chem., 2011, 13, 2320 DOI: 10.1039/C1GC15669A

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