Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates
2019
Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant and trimethylsilyl cyanide as the cyanation reagent. The well streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.
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