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Selective Synthesis of N‑Cyano Sulfilimines by Dearomatizing Stable Thionium Ions

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journal contribution
posted on 22.04.2020, 17:11 by Sang Mee Kim, On-Yu Kang, Hwan Jung Lim, Seong Jun Park
For the selective synthesis of N-cyano sulfilimines, we have developed a new method based on the soft–soft interaction between thionium ion electrophiles and cyanonitrene nucleophiles. The stable thionium ion was successfully obtained by oxidative dearomatization using phenyliodine (III) diacetate (PIDA) in N,N-dimethylformamide (DMF). The sulfur imination reactions were tolerant to a wide range of functional groups and exhibited high selectivities and excellent yields. The existence of thionium ion intermediates was confirmed by ultraviolet/visible (UV/vis) spectroscopy and 1H NMR experiments.