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Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates
- Chen, Yang, Qi, Hongyi, Chen, Ning, Ren, Demin, Xu, Jiaxi, Yang, Zhanhui
- Journal of organic chemistry 2019 v.84 no.14 pp. 9044-9050
- Lewis acids, Lewis bases, cations, chemical reactions, chemical structure, cyanides, dealkylation, organic chemistry, organosilicon compounds, oxidants, sulfur, thiocyanates
- Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the 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.