{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T20:38:25Z","timestamp":1788381505183,"version":"build-2803163510"},"reference-count":73,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2020,10,22]],"date-time":"2020-10-22T00:00:00Z","timestamp":1603324800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A theoretical analysis of the reaction of oxidative sulfamidation of several alkenes was performed in order to explain the various experimental observations and different reactivity of triflamide and non-fluorinated sulfonamides. Transformations occurring in the system alkene\u2013sulfonamide in the presence of oxidative system (ButOCl + NaI) were analyzed at the MP2\/DGDZVP\/\/B3LYP\/DGDZVP level of theory using the IEF-PCM method for taking into account the solvent acetonitrile (MeCN) effect. As the model substrates, styrene, trimethyl(vinyl)silane, dimethyl(divinyl)silane and diphenyl(divinyl)silane were chosen and mesylamide, triflamide, tosylamide and p-nosylamide were taken as the reagents. ButOI generated from ButOCl and NaI reacts with sulfonamides to give N-iodinated sulfonamides RSO2NHI and RSO2NI2 as active intermediates, the iodinating activity of the latter being notably higher. The analysis allowed to answer such challenging questions as different reactivity of nonfluorinated sulfonamides leading to aziridination and of triflamide resulting in the formation the main products of bis-triflamidation, or different regioselectivity of halogenation of styrene and trimethyl(vinyl)silane caused by a linear intermediate iodonium cation in the former case and a cyclic one in the latter.<\/jats:p>","DOI":"10.3390\/molecules25214877","type":"journal-article","created":{"date-parts":[[2020,10,23]],"date-time":"2020-10-23T02:01:42Z","timestamp":1603418502000},"page":"4877","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Trifluoromethanesulfonamide vs. Non-Fluorinated Sulfonamides in Oxidative Sulfamidation of the C=C Bond: An In Silico Study"],"prefix":"10.3390","volume":"25","author":[{"given":"Anton V.","family":"Kuzmin","sequence":"first","affiliation":[{"name":"Siberian Division of Russian Academy of Sciences, A.E. Favorsky Irkutsk Institute of Chemistry, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9460-3413","authenticated-orcid":false,"given":"Mikhail Yu.","family":"Moskalik","sequence":"additional","affiliation":[{"name":"Siberian Division of Russian Academy of Sciences, A.E. Favorsky Irkutsk Institute of Chemistry, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4296-7899","authenticated-orcid":false,"given":"Bagrat A.","family":"Shainyan","sequence":"additional","affiliation":[{"name":"Siberian Division of Russian Academy of Sciences, A.E. Favorsky Irkutsk Institute of Chemistry, 664033 Irkutsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1002\/chin.200545244","article-title":"Catalytic Amination Reactions of Olefins and Alkynes","volume":"36","author":"Beller","year":"2005","journal-title":"Chemin"},{"key":"ref_2","first-page":"2745","article-title":"Recent Development of Regio- and Stereoselective Aminohalogenation Reaction of Alkenes","volume":"38","author":"Li","year":"2007","journal-title":"Chemin"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1172","DOI":"10.1021\/ar900059r","article-title":"Utilization of N\u2212X Bonds in The Synthesis of N-Heterocycles","volume":"42","author":"Minakata","year":"2009","journal-title":"Acc. Chem. 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