{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T08:17:13Z","timestamp":1790929033698,"version":"4.1.0"},"reference-count":74,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2012,12,21]],"date-time":"2012-12-21T00:00:00Z","timestamp":1356048000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The Br\u00f8nsted-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 \u03b1-halo and \u03b1,\u03b1-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of \u03b1-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.<\/jats:p>","DOI":"10.3390\/molecules18010074","type":"journal-article","created":{"date-parts":[[2012,12,21]],"date-time":"2012-12-21T11:06:37Z","timestamp":1356087997000},"page":"74-96","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Br\u00f8nsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)"],"prefix":"10.3390","volume":"18","author":[{"given":"Dejan","family":"Vra\u017ei\u010d","sequence":"first","affiliation":[{"name":"Laboratory for Organic and Bioorganic Chemistry, Jo\u017eef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marjan","family":"Jereb","sequence":"additional","affiliation":[{"name":"Faculty for Chemistry and Chemical Technology, University of Ljubljana, A\u0161ker\u010deva 5, 1000 Ljubljana, Slovenia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenneth","family":"Laali","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University North Florida, Science and Engineering Building, 1 UNF Drive, Jacksonville, FL 32224, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stojan","family":"Stavber","sequence":"additional","affiliation":[{"name":"Laboratory for Organic and Bioorganic Chemistry, Jo\u017eef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia"},{"name":"Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins CIPKeBiP, Jamova 39, 1000 Ljubljana, Slovenia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2012,12,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"354","DOI":"10.1039\/b310389g","article-title":"Iodine electrophiles in stereoselective reactions: ecent developments and synthetic applications","volume":"33","author":"French","year":"2004","journal-title":"Chem. 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