Transition metal-free electrochemical fluorotrifluoromethylation of Styrenes

Abstract

An environmentally-friendly electrochemical fluorotrifluoromethylation of styrenes was developed via the tandem processes of electro-oxidation, radical and nucleophilic addition. By using commercial CF3SO2Na and Et3N·3HF as the CF3 and F source...

Electrochemically Direct Fluorination Functionalization of Styrenes with Different Fluorine Source: Access to Fluoroalkyl Derivatives

“…Upon replacement of the aryl sulfinate with sodium trifluoromethane sulfinate under the optimized condition, the fluorotrifluoromethylation product was formed in good yield ( 3t ) with the trifluoromethane sulfinate acting as a trifluoromethyl radical precursor under oxidative conditions . This is attributed to trifluoromethane sulfinates-based reagents being prone to release SO 2 under oxidative conditions .…”

Electrochemical trifluoroalkylation/annulation for the synthesis of CF3-functionalized tetrahydroquinolines and dihydroquinolinones

“…11 Compared to the classic Umemoto's reagent, Togni's reagent, Ruppert's reagent and Baran's reagent, Langlois’ reagent (NaSO 2 CF 3 ) is a cheaper and easily handled trifluoromethylating reagent. 9 c ,12,13…”

Fluorotrifluoromethylation of Alkenes Mediated by a Hypervalent Trifluoromethyl-Iodine(III) Reagent

“…In 2020, Cui developed a method for the conversion of aliphatic alkenes to the corresponding fluorotrifluoromethylated products mediated by Mn­(OAc) 3 ·2H 2 O with CF 3 SO 2 Na and CF 2 (COOH) 2 . In 2023, Liu and Chen et al presented the electrochemical fluorotrifluoromethylation of styrenes utilizing CF 3 SO 2 Na and Et 3 N·3HF as the CF 3 and F sources, respectively. Although some progress has been made, as mentioned above, the fluorotrifluoromethylation of olefins as a route to polyfluorinated compounds has not yet been fully explored.…”