Molecules 2013, 18(1), 74-96; doi:10.3390/molecules18010074
Article

Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)

1 Laboratory for Organic and Bioorganic Chemistry, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia 2 Faculty for Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia 3 Department of Chemistry, University North Florida, Science and Engineering Building, 1 UNF Drive, Jacksonville, FL 32224, USA 4 Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins CIPKeBiP, Jamova 39, 1000 Ljubljana, Slovenia
* Author to whom correspondence should be addressed.
Received: 15 November 2012; in revised form: 6 December 2012 / Accepted: 11 December 2012 / Published: 21 December 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: The Brønsted-acidic ionic liquid 1-methyl-3-(4-sulfobutyl)imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into α-halo and α,α-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of α-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
Keywords: Brønsted-acidic ionic liquid; halogenation; aromatic ketones; NXS reagents; green chemistry

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MDPI and ACS Style

Vražič, D.; Jereb, M.; Laali, K.K.; Stavber, S. Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS). Molecules 2013, 18, 74-96.

AMA Style

Vražič D, Jereb M, Laali KK, Stavber S. Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS). Molecules. 2013; 18(1):74-96.

Chicago/Turabian Style

Vražič, Dejan; Jereb, Marjan; Laali, Kenneth K.; Stavber, Stojan. 2013. "Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)." Molecules 18, no. 1: 74-96.

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