Green, Scalable, and Low-Cost Synthesis of Fluorine-Containing Bisphenol Monomers through a Synergistic Catalytic System

A facile, green, and scalable synthetic approach for the preparation of structurally diverse fluorine-containing bisphenols has been developed with trifluoroacetaldehyde hydrate that exhibits significant cost advantages. Compared with the conventional harsh conditions with hazardous reagents (using large amounts of anhydrous gaseous HCl/HF or methanesulfonic acid as the reaction medium), the developed method avoids these hazardous reagents and harsh conditions by exploiting the beneficial cooperation of a catalytic amount of TfOH and easily recyclable solvent HFIP, which readily allows hectogram-scale syntheses of fluorine-containing bisphenols. Further mechanistic studies revealed that the synergetic hydrogen bonding interactions between TfOH and HFIP play an important role in promoting this transformation efficiently with enhanced catalytic activity.