Iodine in aqueous micellar environment: a mild effective ecofriendly catalytic system for expedient synthesis of bis(indolyl)methanes and 3-substituted indolyl ketones

The three-component condensation reaction of indoles with carbonyl compounds to yield bis(indolyl)methanes has been accomplished with a catalytic amount of iodine (2 mol%) in the presence of sodium dodecylsulfate (SDS) in aqueous solution above its critical micellar concentration (cmc). The surfacta...

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Bibliographic Details
Published in:Green chemistry letters and reviews 2012-03, Vol.5 (1), p.73-81
Main Authors: Ganguly, Nemai C., Mondal, Pallab, Barik, Sujoy Kumar
Format: Article
Language:English
Subjects:
3-substituted indolyl ketones
Aldehydes
bis(indolyl)methanes
Carbon
iodine
SDS-H
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Summary:The three-component condensation reaction of indoles with carbonyl compounds to yield bis(indolyl)methanes has been accomplished with a catalytic amount of iodine (2 mol%) in the presence of sodium dodecylsulfate (SDS) in aqueous solution above its critical micellar concentration (cmc). The surfactant-aided water-compatible Lewis acid catalyst has been found to be efficient for a wide range of carbonyl compounds including aromatic aldehydes bearing electron-releasing and electron-withdrawing groups, α,β-unsaturated aldehydes, heterocyclic aldehydes, cyclic and aromatic ketones with respect to yield, and reaction time. The protocol has been extended to Michael addition of indoles with α,β-unsaturated ketones exclusively yielding 3-substituted indolyl ketones in excellent yields.
ISSN:1751-8253
1751-7192
DOI:10.1080/17518253.2011.581700