|Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions|
: 101 : 2020.07.04 00:00
|Kim, Sang Mee 2020.05.05|
Selective Synthesis of N-Cyano Sulfilimines by Dearomatizing Stable Thionium Ions
Kim, SM (Kim, Sang Mee)[ 1,3 ] ; Kang, OY (Kang, On-Yu)[ 1,4 ] ; Lim, HJ (Lim, Hwan Jung)[ 1,2 ] ; Park, SJ (Park, Seong Jun)[ 1 ]
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 H-1 NMR experiments.