Choline Hydroxide as a Versatile Medium for Catalyst‐Free O‐Functionalization of Phenols

Abstract

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal-and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

“… 17 Both PFP ( 2 ) and cyanuric fluoride possess aromatic fluorines that are highly susceptible to displacement via S N Ar reactions. Previously, the ability to undergo S N Ar reactions has led to applications for PFP ( 2 ) in protecting group chemistry, 18 peptide modification, 19 unsymmetrical biaryl synthesis, 20 polymer chemistry, 21 and macrocycle synthesis. 22 We speculated that PFP ( 2 ) could be reactive enough to generate acyl fluorides directly from carboxylic acids through an S N Ar, deoxyfluorination sequence.…”