S_NAr Reactions in Ionic Liquids/DES

Mechanism + Description

As per N-based dipolar aprotic solvents

General comments

A number of papers reporting the use of ionic liquids or deep eutectic solvents (DES) as reaction media for S_NAr chemistry have been published, but there does not seem to have been any appreciable uptake by industry. In the case of ionic liquids, concerns around cost, LCA, and ecotoxicity may detract from their use on scale.

Key references

Chemistry Select 2017, 2, 7645-7650 Deep Eutectic Solvent: An Efficient and Recyclable Catalyst for Synthesis of Thioethers.

Chemistry Select 2017, 4892-4898  Deep Eutectic Solvent: An Efficient Catalyst for C‐O Coupling Reactions.

Molecules 2007, 12, 861-867 C(aryl)-O Bond Formation from Aryl Methanesulfonates via Consecutive Deprotection and S_NAr Reactions with Aryl Halides in an Ionic Liquid

Org. Lett., 2009, 11, 5662-5664 Dramatic Effect of Solvent Hydrogen Bond Basicity on the Regiochemistry of S_NAr Reactions of Electron-Deficient Polyfluoroarenes

Org. Lett., Vol. 9, No. 25, 2007 5247-5250  Ionic Liquids as Designer Solvents for Nucleophilic Aromatic Substitutions