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Electrochemical Thiocyanation Utilizing Ammonium Carbamodithioate or NH3·H2O and CS2: A Protocol for Synthesizing
Zan Chen1, Jun-Fa Pang1,2, Shirui Wu1
1College of Chemistry and Civil Engineering, Shaoguan University, Shaoguan 512005, P. R. China.
Abstract:
An iodine-catalyzed electrochemical route for synthesizing thiocyanated heterocycles and aromatics, employing ammonium carbamodithioate or NH3·H2O and CS2 as thiocyanating reagents, has been developed. A variety of thiocyanated indoles, pyrroles, anilines, and anisoles can be selectively obtained in satisfactory yields with good functional group compatibility in aqueous media under air at room temperature. Cyclic voltammograms and control experiments suggest that the transformation proceeds through iodide-induced electrophilic substitution. This strategy features readily available thiocyanating reagents, no external oxidants or transition metals, an aqueous solution, and room temperature conditions.
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