Reducing versus basic properties of 1,2-diaryl-1,2-disodioethanes

The outcome of the reaction between halogenated arylacetic acids and 1,2-diaryl-1,2-disodioethanes strongly depends on the nature of both reaction partners, and it can be rationalized in terms of a competition between reducing and basic properties of the vic-diorganometals, as well as of the ease of the reductive cleavage of the different carbon–halide bonds. As an application of these findings, we developed a particularly mild approach to the synthesis of halogenated and non halogenated α-substituted arylacetic acids.