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

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...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2011-01, Vol.13 (9), p.2320-2325
Main Authors: KUBCZYK, Tomasz M, WILLIAMS, Sarah M, KEAN, Jacqueline R, DAVIES, Thomas E, TAYLOR, Stuart H, GRAHAM, Andrew E
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Colloidal state and disperse state
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Porous materials
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c1gc15669a