Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3

Abstract

The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR₄OCF₃) and pentafluoroethoxide (NR₄OCF₂CF₃) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR₄OCF₃ salts, their long-term stability, and utility in substitution reactions.