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These materials are accessible by nucleophilic ligand substitution at iodine using Me<jats:sub>3<\/jats:sub>SiCF<jats:sub>3<\/jats:sub> in the presence of a substoichiometric amount of fluoride. The expected T\u2010shaped geometry at iodine was verified by X\u2010ray crystallographic analyses of three of the products (1\u2010trifluoromethyl\u20101,2\u2010benziodoxol\u20103\u2010(1\u2009<jats:italic>H<\/jats:italic>)\u2010one and two substituted 1\u2010trifluoromethyl\u20101,3\u2010dihydro\u20101,2\u2010benziodoxoles). Preliminary results for the direct electrophilic transfer of the trifluoromethyl moiety onto organic nucleophiles show modest reactivity in polar aprotic solvents under relatively mild conditions. The overall process can be understood as a formal umpolung of the CF<jats:sub>3<\/jats:sub> group.<\/jats:p>","DOI":"10.1002\/chem.200501052","type":"journal-article","created":{"date-parts":[[2006,1,10]],"date-time":"2006-01-10T05:17:40Z","timestamp":1136870260000},"page":"2579-2586","source":"Crossref","is-referenced-by-count":617,"title":["Novel 10\u2010I\u20103 Hypervalent Iodine\u2010Based Compounds for Electrophilic Trifluoromethylation"],"prefix":"10.1002","volume":"12","author":[{"given":"Patrick","family":"Eisenberger","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sebastian","family":"Gischig","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Togni","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,3]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/352760393X"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-662-04164-2"},{"key":"e_1_2_6_4_2","doi-asserted-by":"crossref","unstructured":"Anon. \u201cFluorine in the life science industry\u201d Chimia2004 58(3) 92\u2013162.","DOI":"10.2533\/000942904777678091"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460441"},{"key":"e_1_2_6_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460441"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200300833"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200301023"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80208-2"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)80011-9"},{"key":"e_1_2_6_11_2","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)88624-X"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)86506-0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/357033a0"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035045u"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.03.072"},{"key":"e_1_2_6_17_2","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)94447-2"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00059a009"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00098a030"},{"key":"e_1_2_6_21_2","first-page":"115","volume":"20","author":"Yagupolskii L. 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