Facile Synthesis of 2-Substituted Benzo[b]thiophen-3-ols in Water

Abstract

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.

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GRAPHICAL ABSTRACT

Keywords:

• Benzo[b]thiophen-3-ol
• DFT
• mechanism
• water-catalyzed

ACKNOWLEDGMENTS

This work was funded by National Natural Science Foundation of China (No. 20802036) and partly by grants from the Specialized Research Fund for the Doctoral Program of Higher Education of China (20070055043) and the Foundation of the Ministry of Education of China for Returned Scholars.

Notes

^a All the reactions were carried out in a hydrothermal bomb for 12 h.

^b The reaction was refluxed for 12 h.

^a All the reactions were carried out by refluxing for 12 h in the presence of zinc powder.