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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, 2, 3 and 1,4,*
Received: 15 November 2012 / Revised: 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 Brønsted-acidic ionic liquid; halogenation; aromatic ketones; NXS reagents; green chemistry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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