The Nucleophilic Substitution of Various Substituted Fluoroarenetricarbonylchromium Complexes with Methoxide

Abstract

The tricarbonylchromium complexes of a variety of di- and trisubstituted fluoro- and difluoroarenes have been reacted in refluxing methoxide/methanol to yield S_NAr-type substitution products. The reaction mixtures were analyzed by glpc and nmr. Methoxide substitution of each fluoride in the complexes occurred rapidly. These are the first examples of the substitution of two fluorides in a tricarbonylchromium complex by a nucleophile. Fluoride was displaced from arenes containing alkyl, methoxy, amino, and alkylamino substituents.