Recyclable Polymer‐Supported Iodobenzene‐Mediated Electrocatalytic Fluorination in Ionic Liquid

Abstract

Abstract:The electrochemical fluorination of organosulfur compounds in triethylamine/hydrofluoric acid (Et 3 N-5 HF) with polystyrene-supported iodobenzene (PSIB) and tetraethylammonium chloride (Et 4 NCl) was performed successfully in an undivided cell under constant current conditions to afford the corresponding fluorinated compounds in moderate to good yields. Recycle use of the PSIB could be achieved due to its easy separation. Notably, the mediatory activity of the iodobenzene derivative was not appreciably changed even after 10 recycle uses.

Fluoro-Pummerer rearrangement and analogous reactions

“…A polymersupported iodobenzene (PSIB) mediator was also effective for indirect anodic fluorination of 53 in HF reagents such as Et 3 NÁ3HF [86] (Scheme 27).…”

Hypervalent Iodine Reagents by Anodic Oxidation: A Powerful Green Synthesis

“…[57,59] Chem.E ur.J. 2018, 24,13399 -13407 www.chemeurj.org In 2010, Fuchigami et al published two reports [61,62] on the indirect anodic fluorinations mediated by recyclable polystyrene-supported iodobenzene 19 and at ask-specific ionic liquid 20 derived from iodophenol (Figure 2).…”

“…[61,62] Scheme9.Indirecta nodicf luorinationo fx anthates 21,p henylsulfides 23 and 25. [61] Figure 3. Use of 20 for indirecta nodicf luorination.…”

Elektrifizierung der organischen Synthese

“…Interestingly,a nisole-derived iodoarenes performed best (Scheme 3). [25,26] Task-specific iodoarenes,carrying,for example,animidazolium moiety, [27] and polymer-supported iodoarenes [28] have also been developed. These are stable during the electrochemical reaction and product extraction, and can be reused in subsequent runs.T hese developments culminated in ahighly selective method for the electrochemical fluorination of (hetero)aromatic compounds under mild reaction conditions.…”