A green solvent approach to the chemistry of 1,2-diaryl-1,2-disodioethanes

We investigated the generation and the reactivity of selected 1,2‐diaryl‐1,2‐disodioethanes employing cyclopentyl methyl ether and 2‐methyltetrahydrofuran as green solvent alternatives to tetrahydrofuran. Both solvents proved suitable for the generation of these vic‐diorganometals, as well as for their employment as single‐electron transfer reagents. On the other hand, 2‐methyltetrahydrofuran appears as the solvent of choice in reactions involving the employment of these diorganometals as nucleophiles or bases. Accordingly, our results disclose an environmentally more sustainable approach to the chemistry of these diorganometals and, in a wider sense, to reductive metalation reactions. Copyright © 2012 John Wiley & Sons, Ltd. CPME and 2‐MeTHF were evaluated as green solvent alternatives to THF in the generation of 1,2‐diaryl‐1,2‐disodiumethanes. Significative differences were observed in the behaviour of these dianions within the two solvents.