Facile synthesis of 2-substituted benzo[b]thiophen-3-ols in water

A facile synthesis of 2-substituted benzo[b]thiophen-3-ols in a simple reaction system is reported with water as the only media. Density functional theory (DFT) investigations suggest two pathways comparable in energetics: A neutral pathway with concerted C-C bond formation and hydrogen transfer and an anionic pathway with anion attack to the carbonyl group. Studies indicate that water plays crucial mechanistic roles in both cases. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.