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We used 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the activating solvent for a nitric acid and FeCl3-catalyzed aerobic oxidation of secondary alcohols to ketones. Reaction proceeded selectively with excellent yields with no reaction on the primary alcohol group. Oxidation of benzyl alcohols proceeds selectively to aldehydes with only HNO3 as the catalyst, while reaction on tertiary alcohols proceeds through dehydration and dimerization. A mechanistic study showed in situ formation of NOCl that converts alcohol into alkyl nitrite, which in the presence of Fe3+ ions and fluorinated alcohol decomposes into ketone. The study indicates that iron(III) acts also as the single-electron transfer catalyst in regeneration of NOCl reactive species.<\/jats:p>","DOI":"10.1021\/acs.joc.9b02109","type":"journal-article","created":{"date-parts":[[2019,10,23]],"date-time":"2019-10-23T14:58:42Z","timestamp":1571842722000},"page":"14579-14586","source":"Crossref","is-referenced-by-count":28,"title":["Aerobic Oxidation of\nSecondary Alcohols with Nitric\nAcid and Iron(III) Chloride as Catalysts in Fluorinated Alcohol"],"prefix":"10.1021","volume":"84","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7416-6981","authenticated-orcid":true,"given":"S\u030ctefan","family":"Moz\u030cina","sequence":"first","affiliation":[{"name":"Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins , Jamova Cesta 39 , ,","place":["Ljubljana, Slovenia, 1000"]},{"name":"Joz\u030cef Stefan International Postgraduate School , Jamova Cesta 39 , ,","place":["Ljubljana, Slovenia, 1000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6340-3577","authenticated-orcid":true,"given":"Jernej","family":"Iskra","sequence":"additional","affiliation":[{"name":"Joz\u030cef Stefan Institute , , Jamova Cesta 39 , ,","place":["Ljubljana, Slovenia, 1000"]},{"name":"University of Ljubljana , , Vec\u030cna Pot 113 , ,","place":["Ljubljana, Slovenia, 1000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,10,23]]},"reference":[{"key":"2026090218444504500_cit1","volume-title":"Oxidation of Alcohols\nto Aldehydes and Ketones: A Guide to Current Common Practice","author":"Tojo","year":"2006"},{"key":"2026090218444504500_cit2","doi-asserted-by":"publisher","first-page":"8824","DOI":"10.1002\/anie.201403110","article-title":"Practical Aerobic\nOxidations of Alcohols and Amines\nwith Homogeneous Copper\/TEMPO and Related Catalyst Systems","volume":"53","author":"Ryland","year":"2014","journal-title":"Angew. 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