Praktičen pristop k deoksifluoriranju elektron-deficitnih fenolov

Jelen, Jan (author), Iskra, Jernej (mentor), Tavčar, Gašper (co-mentor)

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.

• Language: Slovenian
• Keywords: poli(hidrogen fluoridi), deoksifluoriranje, vodni medij, fenoli, elektron-privlačne skupine, enostavno
• Work type: Master's thesis/paper
• Typology: 2.09 - Master's Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-140841
• COBISS.SI-ID: 131900931
• Publication date in RUL: 20.09.2022

Secondary language

• Language: English
• Title: A practical approach to deoxyfluorination of electron-deficient phenols

Abstract

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.

• Keywords: poly(hydrogen fluorides), deoxyfluorination, aqueous media, phenols, electron-withdrawing groups, practical