20.500.12556/RUL-140841 Praktičen pristop k deoksifluoriranju elektron-deficitnih fenolov A practical approach to deoxyfluorination of electron-deficient phenols V tej raziskavi poročamo o praktični in enostavni sintezi deoksifluorirnega reagenta 2-kloro-1,3-bis(2,6-diizopropilfenil)imidazolijevega dihidrogen trifluorida v vodnem mediju pri ambientih pogojih z uporabo hipoklorita in vodne raztopine fluorovodikove kisline. Predstavljen reagent je odporen na zrak in vlago, ter je zmožen pri milih pogojih pretvoriti elektron-deficitne fenole (fenole z elektron-privlačno skupino) v ustrezne aril fluoride ob prisotnosti baze DBU z odličnimi izkoristki. Kaže tudi izjemno toleranco funkcionalnih skupin, kar se je pokazalo na 23 primerih, med katerimi so tudi naravne spojine, barvila in biološko aktivne spojine. Reakcija deoksifluoriranja je enostavna in praktična za izvedbo. Karakterizacija stranskih produktov je omogočala tudi mehanistični vpogled deoksifluoriranja. In this study, we report practical and operationally-friendly synthesis of deoxyfluorination reagent in aqueous media under ambient conditions using hypochlorite as chlorinating agent and hydrofluoric acid as fluoride source. The presented air-stable and moisture-insensitive reagent, based on 2-chloro-1,3-bis(aryl)imidazolium dihydrogen trifluoride, is capable of converting electron-deficient phenols to corresponding aryl fluorides in presence of DBU as a base in excellent yields under mild conditions and great functional group tolerance reflected by 23 examples. Substrate scope include natural occurring compounds, dyes and compounds that exhibit biologically active properties. Deoxyfluorination reaction is simple and practical to perform. Structural characterization of side products also shed light onto mechanistical aspects of deoxyfluorination. poli(hidrogen fluoridi) deoksifluoriranje vodni medij fenoli elektron-privlačne skupine enostavno poly(hydrogen fluorides) deoxyfluorination aqueous media phenols electron-withdrawing groups practical true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2022-09-20 07:25:08 2022-09-20 07:25:17 2022-12-01 13:01:23 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22615 131900931 Jelen_Jan_-_Prakticen_pristop_k_deoksifluoriranju_elektron-deficitnih_fenolov.pdf Jelen_Jan_-_Prakticen_pristop_k_deoksifluoriranju_elektron-deficitnih_fenolov.pdf 1 4F104FB338CA0C2A4C80272D50B56202 c774adb2b7ca1eb53fb937db7b5f779561e2a4d53ca38f47ec9b5e115e676d3f 8d458ed1-38a4-11ed-92af-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=161654 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0