Chemoselective desulfurization-fluorination/bromination of carbonofluoridothioates for the O-trifluoromethylation and O-bromodifluoromethylation of alcohols

摘要

Herein,a method for synthesizing various alkyl trifluoromethyl and alkyl bromodifluoromethyl ethers using carbonofluoridothioates(R-OC(=S)F)as precursors has been described.Carbonofluoridothioates were obtained upon the reaction of an alcohol and S=CF_(2) generated via the decomposition of an SCF_(3) anion,and then selectively transformed into their corresponding trifluoromethyl and bromodifluoromethyl ethers upon changing the reaction conditions.This transformation has also been extended to the one-pot,two-step conversion of alcohols into alkyl trifluoromethyl ethers.A series of alkyl bromodifluoromethyl ethers has also been synthesized.These compounds open up a new avenue for the synthesis of a wide range of useful fluorinated products.In addition,this method is suitable for the late-stage introduction of trifluoromethyl ethers in complex small molecules.