期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 14, 页码 9044-9050出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00965
关键词
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资金
- National Natural Science Foundation of China [21602010]
- Fundamental Research Funds for the Central Universities [XK1802-6, 12060093063]
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.
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